JP2007207961A - Electronic device, substrate therefor, and electronic equipment - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a substrate for an electronic device excellent in carrier transport property, an electronic device excellent in characteristics, and a reliable electronic equipment equipped with the above substrate for the electronic device. <P>SOLUTION: The substrate for an electron device provided for an organic light emitting element 1 comprises a light emitting layer (organic semiconductor layer) 5 consisting of an organic semiconductor material as a main material, an anode (electrode) 7 consisting of an inorganic oxide (except for a silicon oxide) at least in the vicinity of the surface as a main material, and an interlayer 4 consisting of an organic material as a main material which has the function of carrier transport and formed between the light emitting layer 5 and the anode 7. In the vicinity of the interface of the anode 7 and the interlayer 4, the inorganic oxide and the organic material are bonded by the chemical bonding, and this chemical bonding does not contain silicon atoms substantially. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to an electronic device substrate, an electronic device, and an electronic apparatus.

As an electronic device including an organic semiconductor layer and an electrode, and an electronic device substrate provided such that these are in contact with each other, for example, an organic electroluminescence element (hereinafter simply referred to as “organic EL element”). Etc.
This organic EL element is considered to be promising for use as an inexpensive large-area full-color display element (light-emitting element) of a solid light-emitting type, and many developments have been made.

  In general, an organic EL device has a light emitting layer between a cathode and an anode. When an electric field is applied between the cathode and the anode, electrons are injected into the light emitting layer from the cathode side, and holes are formed from the anode side. Is injected.

Then, the injected electrons and holes are recombined in the light emitting layer, and the light emitting layer emits light by releasing the excitation energy when the energy level returns from the conduction band to the valence band as light energy.
In such an organic EL element, in order to increase the efficiency of the organic EL element, that is, to obtain high light emission, an organic semiconductor layer composed of organic semiconductor materials having different electron or hole carrier transport properties is used as a light emitting layer. It has been found that an element structure laminated between the cathode and / or the anode is effective.

Therefore, an organic EL element having a structure in which a light emitting layer and an organic semiconductor layer (hereinafter, collectively referred to as “organic semiconductor layer”) are stacked between an anode and a cathode can obtain high luminous efficiency. For this reason, studies are being made on the molecular structure and molecular aggregation state of organic semiconductor materials, as well as the number and position of organic semiconductor layers to be stacked.
However, even in the organic EL element having such a configuration, the actual situation is that the improvement in characteristics such as light emission efficiency is not expected (see, for example, Patent Document 1).

This is because the interaction between the organic semiconductor materials is larger than the interaction between the organic semiconductor material and the constituent material of the electrode (inorganic material), and the organic semiconductor material and the inorganic material repel each other. It has been found that sufficient adhesion between the electrode and the electrode cannot be obtained, and carriers are not smoothly transferred between these layers.
As a method for solving such a problem, by chemically bonding a silane coupling agent having a carrier transporting portion having a carrier transporting ability to the electrode, the adhesion between the organic semiconductor layer containing the silane coupling agent and the electrode is improved. A method of improving is disclosed (for example, see Patent Document 2).
However, even when such a method is used, carriers (holes or electrons) are trapped by silicon atoms contained in the silane coupling agent, so that carriers are injected from the electrode into the organic semiconductor layer. Is not performed smoothly, and the characteristics of the organic EL element are not sufficiently improved.

Japanese Patent Laid-Open No. 9-255774 JP 2004-307847 A

  An object of the present invention is to provide an electronic device substrate excellent in carrier transport capability, an electronic device excellent in characteristics, and an electronic device having high reliability provided with the electronic device substrate.

Such an object is achieved by the present invention described below.
The substrate for an electronic device of the present invention includes an organic semiconductor layer composed of an organic semiconductor material as a main material,
An electrode composed mainly of an inorganic oxide (excluding silicon oxide) at least near the surface;
An intermediate layer that is provided between the organic semiconductor layer and the electrode and is composed mainly of an organic substance having a function of transporting carriers;
In the vicinity of the interface between the electrode and the intermediate layer, the inorganic oxide and the organic substance are chemically bonded, and the chemical bond is substantially free of silicon atoms.
Thereby, the injection | pouring of the carrier from an electrode to an intermediate | middle layer is performed smoothly, and it can be set as the board | substrate for electronic devices excellent in carrier transport ability.

In the electronic device substrate of the present invention, it is preferable that the organic substance is a compound having a carrier transporting part having a function of transporting carriers and a bonding part for binding the carrier transporting part and the electrode.
In the electronic device substrate according to the present invention, it is preferable that the number of the atoms constituting the bond portion that are linearly connected is 3 to 10.
By setting the number of these linearly linked ones within such a range, the length of the coupling portion is set so that the carrier can be smoothly transferred from the inorganic oxide to the carrier transporting portion, and the inorganic oxide The carrier can be transferred from the carrier to the carrier transport section more smoothly.

In the electronic device substrate of the present invention, it is preferable that the bonding portion includes a hydroxyl group at the terminal.
Thereby, a dehydration reaction can be advanced between the hydroxyl group contained in the terminal of a coupling | bond part and the hydroxyl group exposed from the surface of an electrode, and an inorganic oxide and organic substance can be combined with an ether bond.

In the electronic device substrate of the present invention, the chemical bond is preferably an ether bond.
An ether bond is a chemical bond that is relatively easily formed between hydroxyl groups without substantially containing silicon atoms. Therefore, the bonding rate between the organic substance and the inorganic oxide can be improved. Thereby, the carrier can be more smoothly injected from the electrode to the intermediate layer via the chemical bond (ether bond).
Furthermore, since water generated as a by-product in the dehydration reaction between hydroxyl groups can be removed relatively easily by heating, the by-product is reliably prevented from remaining in the intermediate layer. be able to.

In the electronic device substrate of the present invention, the intermediate layer and the organic semiconductor layer are in contact with each other,
The carrier transport part preferably includes a structure having a high affinity with the organic semiconductor material.
Thereby, the adhesiveness in the interface of an intermediate | middle layer and an organic-semiconductor layer will improve, and the injection efficiency of the carrier from an intermediate | middle layer to an organic-semiconductor layer can be improved.

In the electronic device substrate of the present invention, it is preferable that the carrier transporting portion includes an arylamine skeleton.
Here, as the organic semiconductor material, a compound having a π-electron conjugated structure is preferably used, and the arylamine skeleton has an excellent affinity for this compound. The part exhibits an excellent affinity for the organic semiconductor material. The arylamine skeleton exhibits particularly excellent carrier transport ability. For these reasons, those containing an arylamine skeleton are particularly preferably used as the carrier transporting portion.

［式中、Ｘ^１、Ｘ^２、Ｘ^３およびＸ^４は、それぞれ独立して、水素原子、メチル基、エチル基または下記一般式（Ｂ１）で表される置換基を表し、同一であっても、異なっていてもよい。ただし、Ｘ^１、Ｘ^２、Ｘ^３およびＸ^４のうちの少なくとも１つは、下記一般式（Ｂ１）で表される置換基を表し、その他のものは、水素原子、メチル基またはエチル基を表す。また、８つのＲは、それぞれ独立して、水素原子、メチル基またはエチル基を表し、同一であっても、異なっていてもよく、Ｙは、置換もしくは無置換の芳香族炭化水素環、または、置換もしくは無置換の複素環を少なくとも１つ含む基を表す。］

［式中、ｎは、１〜８の整数を表す。］
これにより、電極から中間層へのキャリアの注入が円滑に行われ、キャリア輸送能に優れた電子デバイス用基板とすることができる。 In the electronic device substrate of the present invention, the organic substance preferably contains a compound represented by the following general formula (A1) as a main component.

[Wherein, X ¹ , X ² , X ³ and X ⁴ each independently represent a hydrogen atom, a methyl group, an ethyl group or a substituent represented by the following general formula (B1), May be different. However, at least one of X ¹ , X ² , X ³ and X ⁴ represents a substituent represented by the following general formula (B1), and the other represents a hydrogen atom, a methyl group or an ethyl group. To express. Eight R's each independently represent a hydrogen atom, a methyl group or an ethyl group, which may be the same or different, and Y is a substituted or unsubstituted aromatic hydrocarbon ring, or Represents a group containing at least one substituted or unsubstituted heterocyclic ring. ]

[Wherein n represents an integer of 1 to 8. ]
Thereby, the injection | pouring of the carrier from an electrode to an intermediate | middle layer is performed smoothly, and it can be set as the board | substrate for electronic devices excellent in carrier transport ability.

In the electronic device substrate of the present invention, it is preferable that each of the substituent X ¹ , the substituent X ² , the substituent X ³ and the substituent X ⁴ represents a substituent represented by the general formula (B1).
Thereby, the main skeleton composed of portions other than the substituent represented by the general formula (B1) can be bonded along the surface of the electrode. As a result, the intermediate layer is formed by laminating the main skeleton so as to overlap the electrode, so that carriers in the intermediate layer can be transferred more smoothly.

In the electronic device substrate of the present invention, the group Y preferably contains at least one substituted or unsubstituted aromatic hydrocarbon ring and is composed of carbon atoms and hydrogen atoms.
Thereby, the compound represented by the general formula (A1) can exhibit hole transporting ability.
In the electronic device substrate of the present invention, the group Y preferably contains at least one substituted or unsubstituted heterocyclic ring.
Thereby, the characteristic of the carrier transport ability in the compound represented by the general formula (A1) can be adjusted more easily.

In the electronic device substrate of the present invention, the intermediate layer preferably has an average thickness of 1 to 50 nm.
By setting the intermediate layer within such a range, it is possible to reliably transfer carriers from the electrode to the organic semiconductor layer via the intermediate layer.
In the electronic device substrate of the present invention, it is preferable that the electrode is subjected to a treatment to increase its surface area.
This increases the surface area of the electrode and increases the number of hydroxyl groups exposed from the electrode. Therefore, it is possible to increase the number of organic substances bonded to the inorganic oxide. As a result, the adhesion between the electrode and the intermediate layer is further improved, and carriers are more smoothly injected from the electrode to the intermediate layer.

The electronic device of the present invention includes the electronic device substrate of the present invention.
Thereby, an electronic device having excellent characteristics can be obtained.
In the electronic device of the present invention, the electronic device is preferably an organic electroluminescence element.
Thereby, the organic EL element excellent in characteristics, such as luminous efficiency, is obtained.
An electronic apparatus according to the present invention includes the electronic device according to the present invention.
Thereby, a highly reliable electronic device can be obtained.

DESCRIPTION OF EMBODIMENTS Hereinafter, a substrate for electronic devices, an electronic device, and an electronic apparatus of the present invention will be described in detail based on preferred embodiments shown in the accompanying drawings.
<Organic electroluminescence device>
First, the case where the electronic device of the present invention is applied to an organic electroluminescence element (hereinafter simply referred to as “organic EL element”) will be described as an example.

FIG. 1 is a longitudinal sectional view showing an example of an organic EL element. In the following description, for convenience of explanation, the upper side in FIG. 1 will be described as “upper” and the lower side as “lower”.
An organic EL element 1 shown in FIG. 1 includes a laminated body 9 including an anode 7, a cathode 3, an intermediate layer 4 that is sequentially laminated between the anode 7 and the cathode 3, and a light emitting layer 5. Is provided. The entire organic EL element 1 is provided on the substrate 2 and sealed with a sealing member 8.
In the present embodiment, in the organic EL element 1, the anode (electrode) 7, the intermediate layer 4, and the light emitting layer (organic semiconductor layer) 5 constitute the electronic device substrate of the present invention.

  The substrate 2 serves as a support for the organic EL element 1. When the organic EL element 1 is configured to extract light from the side opposite to the substrate 2 (top emission type), the substrate 2 and the anode 7 are not particularly required to have transparency. Further, when the organic EL element 1 is configured to extract light from the substrate 2 side (bottom emission type), each of the substrate 2 and the anode 7 is substantially transparent (colorless transparent, colored transparent, translucent). What you have is used.

Examples of the substrate 2 include resin materials such as polyethylene terephthalate, polyethylene naphthalate, polypropylene, cycloolefin polymer, polyamide, polyethersulfone, polymethyl methacrylate, polycarbonate, and polyarylate, and quartz glass and soda glass. Transparent substrate composed of glass material, substrate composed of ceramic material such as alumina, metal substrate such as stainless steel with oxide film (insulating film) formed on it, composed of opaque resin material An opaque substrate such as a patterned substrate can be used.
Although the average thickness of such a board | substrate 2 is not specifically limited, It is preferable that it is about 0.1-10 mm, and it is more preferable that it is about 0.1-5 mm.

The anode 7 is an electrode that injects holes into the intermediate layer 4 described later.
The anode (electrode) 7 is mainly composed of a material having excellent conductivity, and in the present invention, at least the vicinity of the surface thereof is an organic substance having a function of transporting carriers contained in the intermediate layer 4 described later (hereinafter simply referred to as “ It is also called an “organic substance”.) The main material is an inorganic oxide that is bonded with a chemical bond.
The chemical bond formed between these organic substances and inorganic oxide will be described in detail later.

Such an inorganic oxide is not particularly limited as long as it can form a chemical bond with an organic substance and can smoothly inject holes from the anode 7 to the intermediate layer 4. For example, ITO (Indium Tin Oxide), IZO (Indium Zinc Oxide), In ₃ O ₃ , Al ₂ O ₃ , ZnO, SnO ₂ , CeO ₂ , TiO ₂ , CuO, Fe ₂ O ₃ , CoO, V ₂ O ₅ and Y ₂ O ₃ can be used, and one or more of these can be used in combination. However, this inorganic oxide excludes silicon oxide such as SiO ₂ . This is similar to the case where the carrier injection efficiency from the anode (electrode) 7 to the intermediate layer 4 is not improved when silicon atoms are included in the chemical bond formed between the inorganic oxide and the organic substance described later. This is for a reason.

By forming the above-described inorganic oxide as a main material at least near the surface of the anode 7, the anode 7 has a hydroxyl group exposed from the surface. As a result, an organic substance that will be described in detail later can be bonded to the anode 7 through this hydroxyl group by chemical bonding relatively easily.
The average thickness of the anode 7 is not particularly limited, but is preferably about 10 to 200 nm, and more preferably about 50 to 150 nm. If the thickness of the anode 7 is too thin, the function as the anode 7 may not be sufficiently exhibited. On the other hand, if the anode 7 is too thick, electrons and holes are efficiently recombined in the light emitting layer 5. There is a risk that the luminous efficiency of the organic EL element 1 may be reduced.

  Further, the surface resistance of the anode 7 is preferably as low as possible. Specifically, it is preferably 100Ω / □ or less, more preferably 50Ω / □ or less. The lower limit value of the surface resistance is not particularly limited, but is usually preferably about 0.1Ω / □.

On the other hand, the cathode 3 is an electrode for injecting electrons into the light emitting layer 5 described later. As a constituent material of the cathode 3, a material having a small work function is preferably used.
Examples of the constituent material of the cathode 3 include Li, Na, K, Be, Mg, Ca, Sr, Ba, La, Ce, Er, Eu, Sc, Y, Yb, Ag, Cu, Al, Cs, Rb or Examples include alloys containing these, and one or more of these can be used in combination.

In particular, when an alloy is used as the constituent material of the cathode 3, it is preferable to use an alloy containing a stable metal element such as Ag, Al, or Cu, specifically, an alloy such as MgAg, AlLi, CuLi, or LiF. . By using such an alloy as a constituent material of the cathode 3, it is possible to improve the efficiency and stability of electron injection into the light emitting layer 5 described later of the cathode 3.
Although the average thickness of such a cathode 3 is not specifically limited, It is preferable that it is about 1-1000 nm, and it is more preferable that it is about 100-400 nm. If the thickness of the cathode 3 is too thin, the specific resistance increases and a voltage drop may occur, or the electrical conductivity characteristics may become unstable due to an oxidation reaction, and the function as the cathode 3 may not be sufficiently exhibited. On the other hand, when the cathode 3 is too thick, when the cathode 3 is formed by using a vacuum deposition method, a sputtering method, or the like, the temperature in the film is remarkably increased or the residual stress is increased, so that the cathode 3 is provided as a lower layer. The light emitting layer 5 may be destroyed, or the cathode 3 and the light emitting layer 5 may be peeled off, which may reduce the light emission efficiency of the organic EL element 1.

The surface resistance of the cathode 3 is preferably as low as possible. Specifically, it is preferably 50Ω / □ or less, more preferably 20Ω / □ or less. Although the lower limit of the surface resistance is not particularly limited, it is usually preferably about 0.1Ω / □.
In this embodiment, a laminate 9 in which an intermediate layer 4 and a light emitting layer (organic semiconductor layer) 5 are laminated in this order from the anode 7 side between the anode 7 and the cathode 3 is an anode 7 and a cathode. 3 is formed so as to be in contact with 3.

  When energization (voltage is applied) between the anode 7 and the cathode 3, holes move in an intermediate layer 4 to be described later, and electrons move in the light emitting layer 5. Exciton (exciton) is generated by holes and electrons in the vicinity of the interface on the 4 side. This exciton recombines in a certain time, but at this time, the excitation energy accumulated by the exciton generation is mainly emitted as light such as fluorescence or phosphorescence. This is electroluminescence emission.

As a constituent material (light emitting material) of the light emitting layer 5, holes can be injected from the anode 7 side when electrons are applied, and electrons can be injected from the cathode 3 side, thereby providing a field where holes and electrons recombine. A compound having a π-electron conjugated structure is preferably used.
Such light-emitting materials (organic semiconductor materials) include various low-molecular light-emitting materials and various high-molecular light-emitting materials as described below, and at least one of them can be used.

Examples of low-molecular light-emitting materials include benzene compounds such as distyrylbenzene (DSB) and diaminodistyrylbenzene (DADSB), naphthalene compounds such as naphthalene and nile red, and phenanthrene compounds such as phenanthrene. Chrysene, chrysene compounds such as 6-nitrochrysene, perylene, N, N′-bis (2,5-di-t-butylphenyl) -3,4,9,10-perylene-di-carboximide (BPPC) Perylene compounds such as coronene, anthracene compounds such as anthracene and bisstyrylanthracene, pyrene compounds such as pyrene, 4- (di-cyanomethylene) -2-methyl-6 Such as-(para-dimethylaminostyryl) -4H-pyran (DCM) Pyran compounds, acridine compounds such as acridine, stilbene compounds such as stilbene, thiophene compounds such as 2,5-dibenzoxazole thiophene, benzoxazole compounds such as benzoxazole, benzos such as benzimidazole Imidazole compounds, benzothiazole compounds such as 2,2 '-(para-phenylenedivinylene) -bisbenzothiazole, bistyryl (1,4-diphenyl-1,3-butadiene), butadienes such as tetraphenylbutadiene Compounds, naphthalimide compounds such as naphthalimide, coumarin compounds such as coumarin, perinone compounds such as perinone, oxadiazole compounds such as oxadiazole, aldazine compounds, 1, 2, 3 , 4, Cyclopentadiene compounds such as 5-pentaphenyl-1,3-cyclopentadiene (PPCP), quinacridone compounds such as quinacridone and quinacridone red, pyridine compounds such as pyrrolopyridine and thiadiazolopyridine, 2,2 Spiro compounds such as', 7,7'-tetraphenyl-9,9'-spirobifluorene, phthalocyanine (H ₂ Pc), metal or non-metal phthalocyanine compounds such as copper phthalocyanine, florene such as fluorene Compounds, (8-hydroxyquinoline) aluminum (Alq ₃ ), tris (4-methyl-8quinolinolate) aluminum (III) (Almq ₃ ), (8-hydroxyquinoline) zinc (Znq ₂ ), (1,10- Phenanthroline) -tris- (4,4,4-trif Oro-1- (2-thienyl) - butane-1,3-Jioneto) europium _{(III) (Eu (TTA)} 3 (phen)), factory scan (2-phenylpyridine) iridium (Ir _(ppy) 3), Examples include (2, 3, 7, 8, 12, 13, 17, 18-octaethyl-21H, 23H-porphine) various metal complexes such as platinum (II).

  Examples of the polymer light-emitting material include polyacetylene compounds such as trans-type polyacetylene, cis-type polyacetylene, poly (di-phenylacetylene) (PDPA), poly (alkyl, phenylacetylene) (PAPA), and poly (para-para-). Fenvinylene) (PPV), poly (2,5-dialkoxy-para-phenylenevinylene) (RO-PPV), cyano-substituted-poly (para-phenvinylene) (CN-PPV), poly (2-dimethyloctyl) Polyparaphenylene vinylene compounds such as silyl-para-phenylene vinylene (DMOS-PPV), poly (2-methoxy, 5- (2′-ethylhexoxy) -para-phenylene vinylene) (MEH-PPV), poly ( 3-alkylthiophene) (PAT), poly (oxypropylene) Polythiophene compounds such as riol (POPT), poly (9,9-dialkylfluorene) (PDAF), α, ω-bis [N, N′-di (methylphenyl) aminophenyl] -poly [9,9- Bis (2-ethylhexyl) fluorene-2,7-diyl] (PF2 / 6am4), poly (9,9-dioctyl-2,7-divinylenefluorenyl-ortho-co (anthracene-9,10-diyl) Polyfluorene compounds such as poly (para-phenylene) (PPP), polyparaphenylene compounds such as poly (1,5-dialkoxy-para-phenylene) (RO-PPP), poly (N-vinyl) Polycarbazole compounds such as carbazole (PVK), poly (methylphenylsilane) (PMPS), poly (naphthylphenylsilane) PnPs), polysilane-based compounds such as poly (biphenylyl phenyl silane) (pBPS), and the like.

In addition, since the precise | minute light emitting layer 5 is obtained by using a low molecular light emitting material, the light emission efficiency of the light emitting layer 5 improves. Moreover, since the polymer light-emitting material can be dissolved in a solvent relatively easily, the light-emitting layer 5 can be easily formed by various coating methods such as an ink jet printing method.
The thickness (average) of the light emitting layer 5 is not particularly limited, but is preferably about 10 to 150 nm, and more preferably about 50 to 100 nm. By setting the thickness of the light emitting layer 5 within the above range, recombination of holes and electrons is efficiently performed, and the light emission efficiency of the light emitting layer 5 can be further improved.

The intermediate layer 4 has a function of transporting holes injected from the anode 7 to the light emitting layer 5.
Here, in the electronic device of the present invention (an electronic device including the substrate for an electronic device of the present invention), the intermediate layer 4 is composed mainly of an organic substance having a function of transporting carriers, and is connected to the anode (electrode) 7 and the intermediate layer. In the vicinity of the interface with the layer 4, the inorganic oxide constituting the anode 7 and the organic substance form a chemical bond, and this chemical bond is substantially free of silicon atoms.

The structure in which the inorganic oxide and the organic substance are bonded by a chemical bond, that is, the structure in which the anode 7 and the intermediate layer 4 are connected by a chemical bond in the vicinity of the interface, whereby the interface between the anode 7 and the intermediate layer 4 is obtained. Adhesion in the vicinity can be improved.
Furthermore, when a silicon atom is included in a chemical bond formed between an inorganic oxide and an organic substance, carriers (holes in this embodiment) are captured by the silicon atom, and this chemical reaction is caused. Although the carrier injection efficiency from the anode 7 to the intermediate layer 4 through the bond cannot be sufficiently improved, in the electronic device of the present invention, this chemical bond does not substantially contain silicon atoms. Hole injection from the anode 7 to the intermediate layer 4 can be performed smoothly.

In addition, since the organic substance has a function of transporting carriers (holes in the present embodiment), the transport of holes in the intermediate layer 4 can also be performed smoothly.
From these things, the intermediate | middle layer 4 exhibits the outstanding carrier (hole) transport ability. That is, the electronic device substrate exhibits an excellent carrier transport ability.
Such an organic substance is a compound having a carrier transporting part having a function of transporting carriers and a binding part that binds the carrier transporting part and the inorganic oxide (anode 7).

  Here, the length of the bonding portion is set so that the transfer (injection) of carriers (holes) from the inorganic oxide to the carrier transporting portion can be performed smoothly. Among them, the number of linearly linked ones is preferably 3 to 10, more preferably 3 to 5. By setting this number within such a range, delivery (injection) of carriers (holes) from the inorganic oxide (anode 7) to the carrier transport portion can be performed more smoothly.

In addition, the bond portion has a reactive group at its end so that a chemical bond substantially free of silicon atoms can be formed with the inorganic oxide. Although it does not specifically limit as this reactive group, For example, a hydroxyl group, an alkoxide group, a thiol group, a chloride group, etc. are mentioned, Among these, it can use 1 type or in combination of 2 or more types.
By the way, in the present invention, since the anode 7 is mainly composed of the inorganic oxide as described above at least near the surface, the hydroxyl group is exposed from the surface.
Therefore, from the viewpoint of reacting the hydroxyl group with the bonding part, it is preferable to select a bonding part that includes a hydroxyl group at the terminal. Thereby, a dehydration reaction can be advanced between these hydroxyl groups, and an inorganic oxide (anode 7) and organic substance can be combined with an ether bond.

An ether bond is a chemical bond that is relatively easily formed between hydroxyl groups without substantially containing silicon atoms. Therefore, the bonding rate between the organic substance and the inorganic oxide can be improved. Thereby, the injection | pouring of the carrier (hole) from the anode 7 to the intermediate | middle layer 4 via a chemical bond (ether bond) can be performed more smoothly.
Furthermore, since the water produced as a by-product in the dehydration reaction between the hydroxyl groups can be vaporized (removed) relatively easily by heating, a by-product such as a metal salt is present in the intermediate layer 4. It can be reliably prevented from remaining on the surface.

  Next, the carrier transporting portion may be any one having a function of transporting carriers, but has a structure having a high affinity with the light emitting layer (organic semiconductor layer) 5 that contacts the upper side of the intermediate layer 4. It is preferable that it contains. Thereby, the adhesiveness at the interface between the intermediate layer 4 and the light emitting layer 5 is improved, and the injection efficiency of holes (carriers) from the intermediate layer 4 to the light emitting layer 5 can be improved.

Here, as described above, a compound having a π-electron conjugated structure is preferably used as the constituent material (luminescent material) of the light-emitting layer 5, and therefore, this π-electron conjugated structure is used as the carrier transporting portion. And those containing an arylamine skeleton, imidazole skeleton, thiophene skeleton, selenophene skeleton, triazole skeleton, fluorene skeleton, spiro skeleton, oxadiazole skeleton and the like are preferably selected. . Among these, the arylamine skeleton is particularly suitable as a carrier transport portion because it has an excellent affinity for a π-electron conjugated structure and exhibits a particularly excellent carrier transport ability. Used for.
In view of the above, it is preferable that the organic substance contains a compound represented by the following general formula (A1) (hereinafter simply referred to as “compound (A1)”) as a main component.

［式中、Ｘ^１、Ｘ^２、Ｘ^３およびＸ^４は、それぞれ独立して、水素原子、メチル基、エチル基または下記一般式（Ｂ１）で表される置換基を表し、同一であっても、異なっていてもよい。ただし、Ｘ^１、Ｘ^２、Ｘ^３およびＸ^４のうちの少なくとも１つは、下記一般式（Ｂ１）で表される置換基を表し、その他のものは、水素原子、メチル基またはエチル基を表す。また、８つのＲは、それぞれ独立して、水素原子、メチル基またはエチル基を表し、同一であっても、異なっていてもよく、Ｙは、置換もしくは無置換の芳香族炭化水素環、または、置換もしくは無置換の複素環を少なくとも１つ含む基を表す。］

[Wherein, X ¹ , X ² , X ³ and X ⁴ each independently represent a hydrogen atom, a methyl group, an ethyl group or a substituent represented by the following general formula (B1), May be different. However, at least one of X ¹ , X ² , X ³ and X ⁴ represents a substituent represented by the following general formula (B1), and the other represents a hydrogen atom, a methyl group or an ethyl group. To express. Eight R's each independently represent a hydrogen atom, a methyl group or an ethyl group, which may be the same or different, and Y is a substituted or unsubstituted aromatic hydrocarbon ring, or Represents a group containing at least one substituted or unsubstituted heterocyclic ring. ]

［式中、ｎは、１〜８の整数を表す。］

[Wherein n represents an integer of 1 to 8. ]

In the compound (A1), the substituent represented by the above general formula (B1) (hereinafter, simply referred to as “substituent (B1)”) constitutes a bonding part, that is, the main part of the compound (A1). The skeleton constitutes the carrier transport section.
When the substituent (B1) has such a configuration, the hydroxyl group contained in the substituent (B1) and the hydroxyl group exposed at the anode 7 form a chemical bond (ether bond), and substantially contain a silicon atom. And the compound (A1) can be bonded to the inorganic oxide.

  Further, by appropriately setting the number of n in the substituent (B1), it is possible to adjust the number of atoms that are connected in a straight chain among the atoms constituting the connecting portion, and n in the substituent (B1). Is preferably 1 to 8, more preferably 1 to 3. Thereby, delivery (injection) of carriers (holes) from the inorganic oxide to the carrier transport part (main skeleton) can be performed more smoothly.

In addition, the substituent X ¹ , the substituent X ² , the substituent X ³ and the substituent X ⁴ (hereinafter, these may be collectively referred to as “substituent X”) are at least one of these. One is the substituent (B1), but preferably two, more preferably three, and even more preferably four are the substituent (B1).
By constituting the substituent X with the substituent (B1), the main skeleton can be bonded to the inorganic oxide (anode 7) via the substituent (B1), and by increasing the number thereof, The main skeleton can be bonded along the surface of the anode 7. As a result, since the intermediate layer 4 is formed by laminating the main skeleton so as to overlap the anode 7, carriers (holes) in the intermediate layer 4 can be transferred more smoothly.

When a plurality of substituents X are composed of the substituent (B1), n of each substituent (B1) is preferably substantially the same, and more preferably the same. Thereby, since the main skeleton can be reliably bonded along the surface of the anode 7, the above-described effects can be exhibited more remarkably.
The substituent X may be bonded to any position from the 2-position to the 6-position of the benzene ring, but is particularly preferably bonded to any one of the 3-position, 4-position or 5-position. . Thereby, the separation distance between the inorganic oxide and the main skeleton can be maintained at a more appropriate size. As a result, holes can be transferred more smoothly from the inorganic oxide to the main skeleton.

  In addition, among the substituent X, those other than those constituted by the substituent (B1) represent a hydrogen atom, a methyl group or an ethyl group, and these selections are those of n which are constituted by the substituent (B1). What is necessary is just to carry out according to a magnitude | size. For example, when n composed of the substituent (B1) is large, the other is selected as a hydrogen atom, and when n composed of the substituent (B1) is small, otherwise In this case, a methyl group or an ethyl group may be selected.

Next, the main skeleton (carrier transport part) that contributes to the transport of holes (carriers) will be described.
In this main skeleton, the characteristics of the carrier transport ability of the compound (A1) can be changed by appropriately setting the chemical structure of the group (bonding group) Y.
This is because, for example, in the compound (A1), the energy level or band of the valence band and the conduction band of the compound (A1) changes as the electron cloud spread (electron distribution state) in the main skeleton contributing to carrier transport changes. This is considered to be due to a change in the size of the gap (prohibited band width).

  Therefore, the group Y includes at least one substituted or unsubstituted aromatic hydrocarbon ring or substituted or unsubstituted heterocyclic ring. Kinds of these aromatic hydrocarbon rings and / or heterocyclic rings By selecting as appropriate, the characteristics of the carrier transport ability in the compound (A1) can be adjusted relatively easily. In other words, the group Y is selected so that the organic EL element 1 to be obtained can exhibit excellent characteristics according to the type of the constituent material of the light emitting layer 5 and the like.

For example, the compound (A1) obtained by selecting a group (bonding group) Y containing at least one substituted or unsubstituted aromatic hydrocarbon ring and composed of a carbon atom and a hydrogen atom. Can exhibit a hole transporting ability.
Specifically, examples of the structure including at least one unsubstituted aromatic hydrocarbon ring and including a carbon atom and a hydrogen atom include those represented by the following chemical formulas (C1) to (C17). Can be mentioned.

In such a group Y, the total number of carbon atoms is preferably 6-30, more preferably 10-25, and even more preferably 10-20.
Further, in the group Y, the number of aromatic hydrocarbon rings is preferably 1 to 5, more preferably 2 to 5, and even more preferably 2 or 3.
In consideration of these, as the group Y, a biphenylene group represented by the chemical formula (C1) or a derivative thereof is a particularly preferable structure.
By selecting such a group, the hole transport ability of the compound (A1) becomes excellent, and the formed intermediate layer 4 becomes particularly excellent in the hole transport ability.

Next, by selecting a group (bonding group) Y that contains at least one substituted or unsubstituted heterocyclic ring, the characteristics of the carrier transport ability in the resulting compound (A1) can be more easily adjusted. it can.
As such a heterocyclic ring, it is particularly preferable to select one containing at least one heteroatom among nitrogen, oxygen, sulfur, selenium and tellurium. It is particularly easy to change the energy level of the valence band and the conduction band, the band gap (forbidden band width), etc. of the compound (A1) by selecting a heterocycle containing such a heteroatom. It becomes.

The heterocyclic ring may be either aromatic or non-aromatic, but is preferably aromatic. Thereby, it is possible to suitably prevent the deviation of electron density in the chemical structure of the conjugated system of the main skeleton, that is, the localization of π electrons, and to prevent the carrier transport ability of the compound (A1) from being lowered.
The group Y preferably contains 1 to 5 heterocycles that are the same or different, and more preferably contains 1 to 3 heterocycles. If such a number of heterocyclic rings are present in the group Y, the energy level of the valence band and the conduction band of the compound (A1), the size of the band gap (forbidden band width), and the like can be sufficiently changed. .

In addition, the total number of carbon atoms in the group Y is preferably 2 to 75, and more preferably 2 to 50. If the total number of carbon atoms in the group Y is too large, the solubility of the compound (A1) in the solvent may tend to decrease depending on the type of the substituent X.
In addition, by setting the total number of carbon atoms of the group Y within such a range, the planarity in the main skeleton is maintained, so that it is possible to reliably prevent the carrier transport ability in the compound (A1) from being lowered.
In consideration of these, as a structure constituted by an unsubstituted heterocyclic ring, for example, those represented by the following chemical formulas (D1) to (D17) are particularly preferable structures.

［これらの式中、各Ｑ^１は、それぞれ独立して、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表し、同一であっても、異なっていてもよい。各Ｑ^２は、それぞれ独立して、ＳまたはＯを表し、同一であっても、異なっていてもよい。Ｑ^３は、Ｎ−Ｔ^３、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^３は、Ｈ、ＣＨ_３、Ｃ_２Ｈ_５またはＰｈを表す。）を表す。］

[In these formulas, each Q ¹ independently represents NT ¹ , S, O, Se, or Te (where T ¹ represents H, CH ₃ or Ph), and is the same. It may or may not be. Each Q ² independently represents S or O and may be the same or different. Q ³ represents NT ³ , S, O, Se or Te (where T ³ represents H, CH ₃ , C ₂ H ₅ or Ph). ]

Furthermore, by selecting a group (bonding group) Y that includes at least one of a substituted or unsubstituted aromatic hydrocarbon ring and a substituted or unsubstituted heterocyclic ring, Properties can be imparted synergistically.
Such a group Y includes an aromatic hydrocarbon ring directly bonded to each N in the compound (A1) and at least one heterocyclic ring present between these aromatic hydrocarbon rings. Is particularly preferred. Thereby, it is possible to reliably prevent the occurrence of bias in the electron density in the compound (A1). As a result, the carrier transport ability of the compound (A1) becomes uniform.
In consideration of this, as a structure constituted by an unsubstituted aromatic hydrocarbon ring and an unsubstituted heterocyclic ring, for example, those represented by the following chemical formulas (E1) to (E3) are particularly preferable structures. .

［これらの式中、各Ｑ^１は、それぞれ独立して、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表し、同一であっても、異なっていてもよい。］

[In these formulas, each Q ¹ independently represents NT ¹ , S, O, Se, or Te (where T ¹ represents H, CH ₃ or Ph), and is the same. It may or may not be. ]

Thus, by appropriately setting the chemical structure of the group Y, for example, a compound obtained by selecting any one of the chemical formulas (E1), (E3), (D2) and (D16) as the group Y (A1) exhibits particularly excellent hole transport ability.
As described above, the characteristics of the carrier transport ability in the compound (A1) can be adjusted relatively easily by appropriately selecting the type of the aromatic hydrocarbon ring and / or the heterocyclic ring contained in the group Y. The group Y may be selected so that the organic EL element 1 to be obtained can exhibit excellent characteristics according to the type of constituent material of the light emitting layer 5 and the like.

Further, in the unsubstituted aromatic hydrocarbon ring or the unsubstituted heterocyclic ring contained in the group Y, a substituent that does not significantly impair the planarity in the main skeleton may be introduced. Examples of such a substituent include an alkyl group having a relatively small number of carbon atoms such as a methyl group or an ethyl group, a halogen group, and the like.
Further, the substituent R is a hydrogen atom, a methyl group or an ethyl group, and the substituent R is also selected from the substituents X according to the size of n of the substituent X (B1). do it. For example, when n composed of the substituent (B1) is large, a hydrogen atom is selected as the substituent R, and when n composed of the substituent (B1) is small, the substituent As R, a methyl group or an ethyl group may be selected.

  The thickness (average) of the intermediate layer 4 is not particularly limited, but is preferably about 1 to 50 nm, and more preferably about 2 to 20 nm. If the thickness of the intermediate layer 4 is too thin, pinholes are generated, and there is a risk that holes will not be transferred from the anode 7 to the light emitting layer 5 via the intermediate layer 4. On the other hand, when the thickness of the intermediate layer 4 is too thick, the resistance value in the thickness direction of the intermediate layer 4 increases, and the power consumption of the organic EL element 1 increases.

The sealing member 8 is provided so as to cover the anode 7, the intermediate layer 4, the light emitting layer 5, and the cathode 3, and has a function of hermetically sealing them and blocking oxygen and moisture. By providing the sealing member 8, it is possible to suppress or prevent the oxidation of the cathode 3 in particular, and to obtain the effects of improving the reliability of the organic EL element 1 and preventing deterioration / deterioration (improvement of durability).
Examples of the constituent material of the sealing member 8 include Al, Au, Cr, Nb, Ta, Ti, alloys containing these, silicon oxide, various resin materials, and the like.

Further, the sealing member 8 may be formed in a flat plate shape so as to face the substrate 2 and be sealed with a sealing material such as a thermosetting resin.
Such an organic EL element 1 has such a characteristic that when a voltage of 0.5 V is applied so that the cathode 3 is negative and the anode 7 is positive, the resistance value is 100 Ω / cm ² or more. Is preferable, and it is more preferable to have a characteristic of 1 kΩ / cm ² or more. This characteristic indicates that in the organic EL element 1, a short circuit (leakage) between the cathode 3 and the anode 7 is preferably prevented or suppressed, and the organic EL element 1 having such characteristics is provided. Has a particularly high luminous efficiency.

In the present embodiment, the case where the intermediate layer 4 is provided between the anode 7 and the light emitting layer 5 so as to be in contact with both of them has been described. However, the present invention is not limited to such a case. A hole transport layer having a function of transporting holes injected from the intermediate layer 4 to the light emitting layer 5 may be provided between the light emitting layer 4 and the light emitting layer 5.
The constituent material of the hole transport layer may be any material as long as it has a hole transport ability, but various low molecular hole transport materials and various polymer positive materials as shown below. It is preferable that the pore transport material has a basic structure and is a conjugated compound. The conjugated compound is particularly excellent in hole transport capability because it can transport holes very smoothly due to the property of its unique electron cloud spread.

As a low molecular weight hole transport material, 1,1-bis (4-di-para-triaminophenyl) cyclohexane, 1,1′-bis (4-di-para-tolylaminophenyl) -4- Arylcycloalkane 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 (TPD3), 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, N-isopropylcarbazole, carbazole compounds such as N-phenylcarbazole, stilbene, stilbene compounds such as 4-di-para-tolylaminostilbene, O _x Oxazole compounds such as Z, triphenylmethane compounds such as triphenylmethane 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, 2 Oxadiazole compounds such as 1,5-di (4-dimethylaminophenyl) -1,3,4, -oxadiazole, anthracene, anthracene compounds such as 9- (4-diethylaminostyryl) anthracene, fluorenone , 2,4,7-trinitro-9-fluorenone, 2,7-bis (2-hydroxy-3- (2-chlorophenylcarbamoyl) -1-naphthylazo) fluorenone compounds such as fluorenone, anilines such as polyaniline Compounds, silane compounds, Like thiophene, thiophene compounds such as poly (thiophene vinylene), poly (2,2′-thienylpyrrole), 1,4-dithioketo-3,6-diphenyl-pyrrolo- (3,4-c) pyrrolopyrrole Pyrrole compounds, fluorene compounds such as fluorene, porphyrins, porphyrin compounds such as metal tetraphenylporphyrin, quinacridone compounds such as quinacridone, phthalocyanine, copper phthalocyanine, tetra (t-butyl) copper phthalocyanine, iron phthalocyanine Metal or metal-free phthalocyanine compounds such as copper naphthalocyanine, vanadyl naphthalocyanine, metal or metal-free naphthalocyanine compounds such as monochlorogallium naphthalocyanine, N, N′-di (naphthalen-1-yl) -N N'- diphenyl - benzidine, N, N, N ', benzidine-based compounds such as N'- tetraphenyl benzidine and the like may be used singly or in combination of two or more of them. All of these have a high hole transport ability.

As a polymer hole transport material, it can be used as a prepolymer or polymer (polymer hole transport material) having the monomer or oligomer (low molecular hole transport material) compound in the main chain or side chain. .
Further, an electron transport layer having a function of transporting electrons injected from the cathode 3 to the light emitting layer 5 may be provided between the cathode 3 and the light emitting layer 5.

The constituent material (electron transport material) of the electron transport layer is not particularly limited. For example, 1,3,5-tris [(3-phenyl-6-tri-fluoromethyl) quinoxalin-2-yl] benzene (TPQ1) ), 1,3,5-tris [{3- (4-t-butylphenyl) -6-trisfluoromethyl} quinoxalin-2-yl] benzene (TPQ2) (starburst compound) , Naphthalene compounds such as naphthalene, phenanthrene compounds such as phenanthrene, chrysene compounds such as chrysene, perylene compounds such as perylene, anthracene compounds such as anthracene, pyrene compounds such as pyrene, acridine Acridine compounds such as stilbene compounds such as stilbene, BBOT Thiophene compounds, butadiene compounds such as butadiene, coumarin compounds such as coumarin, quinoline compounds such as quinoline, bistyryl compounds such as bistyryl, pyrazine compounds such as pyrazine and distyrylpyrazine, Quinoxaline compounds such as quinoxaline, benzoquinone, benzoquinone compounds such as 2,5-diphenyl-para-benzoquinone, naphthoquinone compounds such as naphthoquinone, anthraquinone compounds such as anthraquinone, oxadiazole, 2- (4 -Biphenylyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole (PBD), oxadiazole compounds such as BMD, BND, BDD, BAPD, triazole, 3,4, 5-triphenyl-1,2 Triazole compounds such as 4-triazole, oxazole compounds, anthrone compounds such as anthrone, fluorenone, fluorenone compounds such as 1,3,8-trinitro-fluorenone (TNF), diphenoquinone, diphenoquinone such as MBDQ Compound, stilbene quinone, stilbene quinone compound such as MBSQ, anthraquinodimethane compound, thiopyran dioxide compound, fluorenylidene methane compound, diphenyldicyanoethylene compound, fluorene compound such as fluorene, phthalocyanine, copper phthalocyanine, metal or metal-free phthalocyanine compound such as iron phthalocyanine, (8-hydroxyquinoline) aluminum (Alq _3), benzoxazole or Benzochiazo Various metal complexes such as complexes having a ligand, and the like, can be used at least one of them.

Further, when the cathode 3 is replaced with the constituent materials as described above and the inorganic oxide described in the anode 7 is formed at least near the surface, an intermediate layer is provided between the cathode 3 and the light emitting layer 5. You may do it. That is, the electronic device substrate of the present invention may be constituted by the cathode (electrode) 3, the intermediate layer, and the light emitting layer (organic semiconductor layer) 5.
In this case, a carrier transport part having a function of transporting carriers is preferably selected to have an excellent electron transport ability. Therefore, when using the compound (A1) as the organic substance, it is preferable to select any one of the chemical formulas (D7), (E2), and (D17) as the group Y. By selecting the chemical formula having such a chemical formula as the group Y, the resulting compound (A1) exhibits particularly excellent electron transport ability.

Such an organic EL element 1 can be manufactured as follows, for example.
[1A] Anode Formation Step First, the substrate 2 is prepared, and the anode 7 is formed on the substrate 2.
The anode 7 is, for example, a chemical vapor deposition method (CVD) such as plasma CVD, thermal CVD, or laser CVD, a dry plating method such as vacuum deposition, sputtering, or ion plating, or a wet method such as electrolytic plating, immersion plating, or electroless plating. It can be formed by using one or a combination of two or more of plating methods, thermal spraying methods, sol-gel methods, MOD methods, metal foil bonding, and the like.

The anode 7 may be subjected to a treatment for increasing its surface area. By increasing the surface area of the anode 7, the number of hydroxyl groups exposed from the anode 7 increases. Therefore, when the intermediate layer 4 is formed in the next step [2A], the number of organic substances bonded to the inorganic oxide is reduced. Can be increased. As a result, the adhesion between the anode 7 and the intermediate layer 4 is further improved, and carriers (holes) are more smoothly injected from the anode 7 into the intermediate layer 4.
A method for increasing the surface area of the anode 7 is not particularly limited. For example, a method for forming the surface of the anode 7 with a porous film, a method for rubbing the surface of the anode 7, and an anode for oxidizing the surface of the anode 7. Examples thereof include an oxidation method.

[2A] Intermediate Layer Forming Step [2A-1] First, an intermediate layer forming material containing an organic substance having a function of transporting carriers is applied (supplied) onto the anode 7.
For this coating, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, Various coating methods such as an offset printing method and an ink jet printing method can be used. According to such a coating method, the intermediate layer forming material can be supplied onto the anode 7 relatively easily.

  When an organic substance is dissolved in a solvent or dispersed in a dispersion medium, examples of the solvent or dispersion medium to be used include inorganic solvents such as nitric acid, sulfuric acid, ammonia, hydrogen peroxide, water, carbon disulfide, carbon tetrachloride, and ethylene carbonate, , Ketone solvents such as methyl ethyl ketone (MEK), acetone, diethyl ketone, methyl isobutyl ketone (MIBK), methyl isopropyl ketone (MIPK), cyclohexanone, alcohols such as methanol, ethanol, isopropanol, ethylene glycol, diethylene glycol (DEG), glycerin Solvents, diethyl ether, diisopropyl ether, 1,2-dimethoxyethane (DME), 1,4-dioxane, tetrahydrofuran (THF), tetrahydropyran (THP), anisole, diethylene glycol Ether solvents such as methyl ether (diglyme), diethylene glycol ethyl ether (carbitol), cellosolv solvents such as methyl cellosolve, ethyl cellosolve, phenyl cellosolve, aliphatic hydrocarbon solvents such as hexane, pentane, heptane, cyclohexane, toluene , Aromatic hydrocarbon solvents such as xylene and benzene, aromatic heterocyclic compounds solvents such as pyridine, pyrazine, furan, pyrrole, thiophene and methylpyrrolidone, N, N-dimethylformamide (DMF), N, N-dimethyl Amide solvents such as acetamide (DMA), halogen compound solvents such as dichloromethane, chloroform, 1,2-dichloroethane, ester solvents such as ethyl acetate, methyl acetate, ethyl formate, dimethyl sulfoxide (DMSO), sulfora Various organic solvents such as sulfur compound solvents such as nitrile solvents such as acetonitrile, propionitrile and acrylonitrile, organic acid solvents such as formic acid, acetic acid, trichloroacetic acid and trifluoroacetic acid, or mixed solvents containing these Etc.

[2A-2] Next, the intermediate layer forming material supplied on the anode 7 is subjected to a predetermined treatment.
As a result, the organic substance contained in the intermediate layer forming material is bonded to the inorganic oxide present near the surface of the anode 7 by a chemical bond, and the intermediate layer 4 is formed on the anode 7.
The predetermined treatment applied to the intermediate layer forming material is not particularly limited, and examples thereof include heat treatment, infrared irradiation treatment, ultraviolet irradiation treatment, and microwave treatment. When the compound (A1) is used as an organic substance, It is preferable to select a heat treatment. According to the heat treatment, the dehydration reaction proceeds between the hydroxyl group exposed on the surface of the anode 7 and the hydroxyl group present at the terminal of the substituent (B1), and an ether bond is formed relatively easily. The compound (A1) can be bonded to the oxide (anode 7).

The temperature during the heat treatment is preferably about 80 to 250 ° C, and more preferably about 100 to 200 ° C.
Moreover, it is preferable that the heat time of heat processing is about 20 to 180 minutes, and it is more preferable that it is about 40 to 100 minutes.
By setting the temperature and the heating time of the heat treatment to such ranges, the rate at which an ether bond is formed between the inorganic oxide and the compound (A1) can be controlled relatively easily.

Note that the obtained intermediate layer 4 may be subjected to a second heat treatment, for example, in the air, in an inert atmosphere, or under reduced pressure (or vacuum), if necessary. Thereby, for example, the intermediate layer 4 can be dried (desolvent or dedispersion medium), solidified, and the like. The intermediate layer 4 may be dried regardless of the second heat treatment.
Further, after the organic substance is bonded to the inorganic oxide near the surface of the anode 7, the organic substance not bonded to the inorganic oxide may be dissolved in a solvent that can be dissolved and removed from the intermediate layer 4. .

[3A] Light-Emitting Layer Formation Step Next, the light-emitting layer 5 is formed on the intermediate layer 4, that is, on the surface of the intermediate layer 4 opposite to the anode 7.
For example, after the light emitting layer forming material obtained by dissolving the light emitting material as described above in a solvent or dispersing in a dispersion medium is applied (supplied) onto the intermediate layer 4, the light emitting layer 5 It can be obtained by removing the contained solvent or dispersion medium.
As the method for supplying the light emitting layer forming material onto the intermediate layer 4 and the solvent or dispersion medium, the same ones as described in the above step [2A] can be used.

[4A] Cathode Formation Step Next, the cathode 3 is formed on the light emitting layer 5.
The cathode 3 can be formed using, for example, a vacuum deposition method, a sputtering method, a metal foil bonding, or the like.
[5A] Sealing Member Forming Step Next, the sealing member 8 is formed so as to cover the anode 7, the intermediate layer 4, the light emitting layer 5, and the cathode 3.

The sealing member 8 can be formed (provided), for example, by bonding a box-shaped protective cover made of the above-described material with various curable resins (adhesives).
As the curable resin, any of a thermosetting resin, a photocurable resin, a reactive curable resin, and an anaerobic curable resin can be used.
The organic EL element 1 is manufactured through the above processes.

In the present embodiment, the case where the organic EL element 1 is manufactured by sequentially laminating the intermediate layer 4, the light emitting layer 5, the hole transport layer, and the anode 7 on the cathode 3 has been described. The case is not limited.
For example, a laminate in which the intermediate layer 4 is formed on the anode 7 and a laminate in which the light emitting layer 5 is laminated on the cathode 3 are prepared, and the intermediate layer 4 and the light emitting layer 5 are opposed to each other. Thus, they may be manufactured by bringing them into contact with each other and bonding them together.
The organic EL element 1 can be used, for example, for a display device, but can also be used as a light source or the like, and can be used for various optical applications.

When the organic EL element 1 is used for a display device, a plurality of organic EL elements 1 are provided in the display device. Examples of such a display device include the following.
FIG. 2 is a longitudinal sectional view showing a display device including a plurality of organic EL elements.
A display device 100 shown in FIG. 2 includes a base 20 and a plurality of organic EL elements 1 provided on the base 20.

The base body 20 includes a substrate 21 and a circuit unit 22 formed on the substrate 21.
The circuit unit 22 includes a protective layer 23 made of, for example, a silicon oxide layer formed on the substrate 21, a driving TFT (switching element) 24 formed on the protective layer 23, a first interlayer insulating layer 25, And a second interlayer insulating layer 26.
The driving TFT 24 includes a semiconductor layer 241 made of silicon, a gate insulating layer 242 formed on the semiconductor layer 241, a gate electrode 243 formed on the gate insulating layer 242, a source electrode 244, and a drain electrode 245. have.
On such a circuit portion 22, the organic EL elements 1 are provided corresponding to the respective driving TFTs 24. Adjacent organic EL elements 1 are partitioned by a first partition wall 31 and a second partition wall 32.

In the present embodiment, the anode 7 of each organic EL element 1 constitutes a pixel electrode and is electrically connected to the drain electrode 245 of each driving TFT 24 by the wiring 27. The cathode 3 of each organic EL element 1 is a common electrode.
And the sealing member (not shown) is joined to the base | substrate 20 so that each organic EL element 1 may be covered, and each organic EL element 1 is sealed.
The display device 100 may be monochromatic display, and color display is also possible by selecting a light emitting material used for each organic EL element 1.

<Electronic equipment>
The organic EL element 1 (the electronic device of the present invention) as described above can be incorporated into various electronic devices.
FIG. 3 is a perspective view showing the configuration of a mobile (or notebook) personal computer to which the electronic apparatus of the present invention is applied.

In this figure, a personal computer 1100 includes a main body 1104 provided with a keyboard 1102 and a display unit 1106 provided with a display. The display unit 1106 is rotatable with respect to the main body 1104 via a hinge structure. It is supported by.
In the personal computer 1100, the display unit included in the display unit 1106 includes the organic EL element 1 described above.

FIG. 4 is a perspective view showing a configuration of a mobile phone (including PHS) to which the electronic apparatus of the present invention is applied.
In this figure, a cellular phone 1200 includes a plurality of operation buttons 1202, an earpiece 1204 and a mouthpiece 1206, and a display unit.
In the mobile phone 1200, the display unit includes the organic EL element 1 described above.

FIG. 5 is a perspective view showing a configuration of a digital still camera to which the electronic apparatus of the present invention is applied. In this figure, connection with an external device is also simply shown.
Here, an ordinary camera sensitizes a silver halide photographic film with a light image of a subject, whereas a digital still camera 1300 photoelectrically converts a light image of a subject with an imaging device such as a CCD (Charge Coupled Device). An imaging signal (image signal) is generated.

A display unit is provided on the back of a case (body) 1302 in the digital still camera 1300, and is configured to display based on an imaging signal from the CCD, and functions as a finder that displays an object as an electronic image.
In the digital still camera 1300, the display unit includes the organic EL element 1 described above.

A circuit board 1308 is installed inside the case. The circuit board 1308 is provided with a memory that can store (store) an imaging signal.
A light receiving unit 1304 including an optical lens (imaging optical system), a CCD, and the like is provided on the front side of the case 1302 (on the back side in the illustrated configuration).
When the photographer confirms the subject image displayed on the display unit and presses the shutter button 1306, the CCD image pickup signal at that time is transferred and stored in the memory of the circuit board 1308.

  In the digital still camera 1300, a video signal output terminal 1312 and an input / output terminal 1314 for data communication are provided on the side surface of the case 1302. As shown in the figure, a television monitor 1430 is connected to the video signal output terminal 1312 and a personal computer 1440 is connected to the data communication input / output terminal 1314 as necessary. Further, the imaging signal stored in the memory of the circuit board 1308 is output to the television monitor 1430 or the personal computer 1440 by a predetermined operation.

  The electronic apparatus of the present invention includes, for example, a television, a video camera, a viewfinder type, in addition to the personal computer (mobile personal computer) in FIG. 3, the mobile phone in FIG. 4, and the digital still camera in FIG. Monitor direct-view video tape recorder, laptop personal computer, car navigation system, pager, electronic notebook (including communication function), electronic dictionary, calculator, electronic game device, word processor, workstation, video phone, security TV Monitors, electronic binoculars, POS terminals, devices equipped with touch panels (for example, cash dispensers and automatic ticket vending machines for financial institutions), medical devices (for example, electronic thermometers, blood pressure monitors, blood glucose meters, electrocardiographs, ultrasound diagnostic devices, internal Endoscope display device), fish finder, various measuring instruments, Vessels such (e.g., gages for vehicles, aircraft, and ships), a flight simulator, various monitors, and a projection display such as a projector.

As mentioned above, although the board | substrate for electronic devices, the electronic device, and the electronic device of this invention were demonstrated based on embodiment of illustration, this invention is not limited to these.
For example, the electronic device of the present invention provided with the substrate for an electronic device of the present invention can be applied to the above-described organic EL element, and also applied to, for example, a photoelectric conversion element, a laser element, a printer head element, a white light emitting element, etc. can do.

Next, specific examples of the present invention will be described.
1. Synthesis of compounds First, compounds (A) to (J) as shown below were prepared.
<Compound (A)>
6- (p-aminophenyl) hexanol was treated with 4-methoxybenzyl bromide and sodium hydride in anhydrous dimethylformamide to convert and protect the hydroxyl group to a benzyl ether group.

Next, 1 mol of the obtained compound was dissolved in 150 mL of acetic acid, and acetic anhydride was added dropwise at room temperature, followed by stirring. After completion of the reaction, the precipitated solid was filtered, washed with water and dried.
Next, 0.37 mol of the obtained substance, 0.66 mol of 1-bromo-4-hexylbenzene, 1.1 mol of potassium carbonate, copper powder and iodine were mixed and heated at 200 ° C. After allowing to cool, 130 mL of isoamyl alcohol, 50 mL of pure water, and 0.73 mol of potassium hydroxide were added and the mixture was stirred and dried.

Further, 130 mmol of the compound obtained there, 62 mmol of 4,4′-diiodobiphenyl, 1.3 mmol of palladium acetate, 5.2 mmol of t-butylphosphine, 260 mmol of t-butoxynatrim and 700 mL of xylene were mixed and stirred at 120 ° C. did.
Then, it stood to cool and crystallized.
The obtained compound was reduced with hydrogen gas under a Pd—C catalyst, converted from a benzyl ether group to a hydroxyl group, deprotected, then allowed to cool and crystallized to obtain a compound.
And mass spectrum (MS) method, ¹ H-nuclear magnetic resonance ( ¹ H-NMR) spectrum method, ¹³ C-nuclear magnetic resonance ( ¹³ C-NMR) spectrum method, and Fourier transform infrared absorption (FT-IR) It was confirmed by a spectral method that the obtained compound was the following compound (A).

<Compound (B)>
6- (p-aminophenyl) hexanol was treated with 4-methoxybenzyl bromide and sodium hydride in anhydrous dimethylformamide to convert and protect the hydroxyl group to a benzyl ether group.
Next, 1 mol of the obtained compound was dissolved in 150 mL of acetic acid, and acetic anhydride was added dropwise at room temperature, followed by stirring. After completion of the reaction, the precipitated solid was filtered, washed with water and dried.
Next, a dried product (benzyl ether derivative) obtained by converting hydroxyl group to benzyl ether group from 6- (p-bromophenyl) hexanol by the same treatment as that applied to 6- (p-aminophenyl) hexanol. )

  Next, 0.37 mol of benzyl ether derivative obtained from 6- (p-aminophenyl) hexanol, 0.66 mol of benzyl ether derivative obtained from 6- (p-bromophenyl) hexanol, 1.1 mol of potassium carbonate, copper Powder and iodine were mixed and heated at 200 ° C. After allowing to cool, 130 mL of isoamyl alcohol, 50 mL of pure water, and 0.73 mol of potassium hydroxide were added and the mixture was stirred and dried.

Further, 130 mmol of the compound obtained there, 62 mmol of 4,4′-diiodobiphenyl, 1.3 mmol of palladium acetate, 5.2 mmol of t-butylphosphine, 260 mmol of t-butoxynatrim and 700 mL of xylene were mixed and stirred at 120 ° C. did. Then, it stood to cool and crystallized.
The obtained compound was reduced with hydrogen gas under a Pd—C catalyst, converted from a benzyl ether group to a hydroxyl group, deprotected, then allowed to cool and crystallized to obtain a compound.
And mass spectrum (MS) method, ¹ H-nuclear magnetic resonance ( ¹ H-NMR) spectrum method, ¹³ C-nuclear magnetic resonance ( ¹³ C-NMR) spectrum method, and Fourier transform infrared absorption (FT-IR) It was confirmed by a spectral method that the obtained compound was the following compound (B).

<Compound (C)>
Except for using 1- (p-aminophenyl) methanol instead of 6- (p-aminophenyl) hexanol and using 1-bromo-4-methylbenzene instead of 1-bromo-4-hexylbenzene. Compound (C) was obtained in the same manner as Compound (A).

<Compound (D)>
Except for using 3- (p-aminophenyl) propanol in place of 6- (p-aminophenyl) hexanol and using 1-bromo-4-propylbenzene in place of 1-bromo-4-hexylbenzene. Compound (D) was obtained in the same manner as Compound (A).

<Compound (E)>
Except that 4- (p-aminophenyl) butanol was used instead of 6- (p-aminophenyl) hexanol and 1-bromo-4-butylbenzene was used instead of 1-bromo-4-hexylbenzene. Compound (E) was obtained in the same manner as Compound (A).

<Compound (F)>
Except that 8- (p-aminophenyl) octanol was used instead of 6- (p-aminophenyl) hexanol and 1-bromo-4-octylbenzene was used instead of 1-bromo-4-hexylbenzene. Compound (F) was obtained in the same manner as Compound (A).

<Compound (G)>
Compound (G) was obtained in the same manner as Compound (A) except that 2,5-bis (4-iodophenyl) -thiophene was used instead of 4,4′-diiodobiphenyl.

<Compound (H)>
Compound (H) was obtained in the same manner as Compound (A) except that 3,5-diiodo-1,2,4-triazole was used in place of 4,4′-diiodobiphenyl.

<Compound (I)>
First, p-terphenyl was dissolved in carbon tetrachloride and brominated using 2,2′-azobisisobutyronitrile and N-bromosuccinimide to obtain 1-bromo-p-terphenyl. .
Next, 1-bromo-p-terphenyl is dissolved in toluene, and while stirring the resulting solution, silicon tetrachloride gas in the presence of nitrogen gas is supplied to this solution and then dried to obtain a compound. It was.
And mass spectrum (MS) method, ¹ H-nuclear magnetic resonance ( ¹ H-NMR) spectrum method, ¹³ C-nuclear magnetic resonance ( ¹³ C-NMR) spectrum method, and Fourier transform infrared absorption (FT-IR) It was confirmed by a spectral method that the obtained compound was terphenyltrichlorosilane represented by the following compound (I).

<Compound (J)>
As the following compound (J), N, N, N ′, N′-tetrakis (4-methylphenyl) -benzidine (“OSA6140” manufactured by Tosco Corporation) was prepared.

2. Manufacture of an organic EL element Five organic EL elements were manufactured in each of the following Examples and Comparative Examples.
Example 1
[Preparation of intermediate layer forming material]
Compound (A) was prepared as an organic substance, and compound (A) was dissolved in xylene to obtain an intermediate layer forming material.

[Production of organic EL element]
-1A- First, a transparent glass substrate having an average thickness of 0.5 mm was prepared, and an ITO electrode (anode) having an average thickness of 100 nm was formed on the glass substrate by vacuum deposition.
-2A- Next, the intermediate layer forming material prepared above was applied (supplied) onto the ITO electrode by a spin coating method.
Thereafter, the intermediate layer-forming material is heated and dried under an atmospheric pressure atmosphere at 150 ° C. for 40 minutes, whereby the compound (A) is ether-bonded to the ITO electrode, and an intermediate layer having an average thickness of 10 nm is obtained. Formed.

-3A- Next, 1. poly (9,9-dioctyl-2,7-divinylenefluorenyl-ortho-co (anthracene-9,10-diyl) (weight average molecular weight 200000) on the intermediate layer. A 7 wt% xylene solution was applied by spin coating and then dried to form a light emitting layer having an average thickness of 50 nm.
-4A- Next, an AlLi electrode (cathode) having an average thickness of 300 nm was formed on the light emitting layer by vacuum deposition.
-5A- Next, a protective cover made of polycarbonate was placed so as to cover each formed layer, and fixed and sealed with an ultraviolet curable resin to complete an organic EL element.

(Example 2)
An organic EL device was manufactured after preparing an intermediate layer forming material in the same manner as in Example 1 except that the compound (B) was used as the organic substance.
(Example 3)
An organic EL device was manufactured after preparing an intermediate layer forming material in the same manner as in Example 1 except that the compound (E) was used as the organic material.

Example 4
An organic EL device was manufactured after preparing an intermediate layer forming material in the same manner as in Example 1 except that the compound (F) was used as the organic substance.
(Example 5)
An organic EL device was manufactured after preparing an intermediate layer forming material in the same manner as in Example 1 except that the compound (C) was used as the organic substance.

(Example 6)
An organic EL element was manufactured after preparing an intermediate layer forming material in the same manner as in Example 1 except that the compound (D) was used as the organic substance.
(Example 7)
An organic EL element was manufactured after preparing an intermediate layer forming material in the same manner as in Example 1 except that the compound (G) was used as the organic substance.

(Example 8)
[Preparation of intermediate layer forming material]
The compound (H) was prepared as an organic substance, and the compound (H) was dissolved in xylene to obtain an intermediate layer forming material.
[Production of organic EL element]
-1B- First, a transparent glass substrate having an average thickness of 0.5 mm was prepared, and an ITO electrode (cathode) having an average thickness of 100 nm was formed on the glass substrate by vacuum deposition.
-2B- Next, the intermediate layer forming material prepared above was applied (supplied) onto the cathode by a spin coating method.
Thereafter, the intermediate layer-forming material is heated and dried under an atmospheric pressure atmosphere at 150 ° C. for 40 minutes to ether bond the compound (H) to the ITO electrode (cathode), resulting in an average thickness of 10 nm. An intermediate layer was formed.

-3B- Next, 1. poly (9,9-dioctyl-2,7-divinylenefluorenyl-ortho-co (anthracene-9,10-diyl) (weight average molecular weight 200000) on the intermediate layer. A 7 wt% xylene solution was applied by spin coating and then dried to form a light emitting layer having an average thickness of 50 nm.
-4B- Next, an ITO electrode (cathode) having an average thickness of 100 nm was formed on the light emitting layer in the same manner as in Step-1B-.
-5B- Next, a protective cover made of polycarbonate was placed so as to cover each formed layer, and fixed and sealed with an ultraviolet curable resin, thereby completing an organic EL element.

Example 9
[Preparation of first intermediate layer forming material]
The compound (A) was prepared as an organic substance, and the compound (A) was dissolved in xylene to obtain a first intermediate layer forming material.
[Preparation of Second Intermediate Layer Forming Material]
A compound (H) was prepared as an organic substance, and the compound (H) was dissolved in xylene to obtain a second intermediate layer forming material.

[Production of organic EL element]
-1C- First, a transparent glass substrate having an average thickness of 0.5 mm was prepared, and an ITO electrode (anode) having an average thickness of 100 nm was formed on the glass substrate by a vacuum deposition method.
-2C- Next, the first intermediate layer forming material prepared in advance was applied (supplied) onto the ITO electrode by a spin coating method.
Thereafter, the first intermediate layer-forming material is heated and dried under an atmospheric pressure atmosphere at 150 ° C. for 40 minutes, whereby the compound (A) is ether-bonded to the ITO electrode, and the average thickness is 10 nm. The first intermediate layer was formed.

-3C- Next, on the first intermediate layer, poly (9,9-dioctyl-2,7-divinylenefluorenyl-ortho-co (anthracene-9,10-diyl) (weight average molecular weight 200000) A 1.7 wt% xylene solution was applied by spin coating and then dried to form a first coating film.
-4C- Next, a transparent glass substrate having an average thickness of 0.5 mm was prepared, and an ITO electrode (cathode) having an average thickness of 100 nm was formed on the glass substrate by vacuum deposition.

-5C- Next, the second intermediate layer forming material prepared in advance was applied (supplied) onto the cathode by a spin coating method.
Thereafter, the second intermediate layer forming material is heated and dried under an atmospheric pressure atmosphere at 150 ° C. for 40 minutes, whereby the compound (H) is ether-bonded to the ITO electrode (cathode) and averaged. A second intermediate layer having a thickness of 10 nm was formed.

-6C- Next, on the second intermediate layer, poly (9,9-dioctyl-2,7-divinylenefluorenyl-ortho-co (anthracene-9,10-diyl) (weight average molecular weight 200000) A 1.7 wt% xylene solution was applied by spin coating and then dried to form a second coating film.
-7C- Next, the glass substrate provided with the first coating film and the glass substrate provided with the second coating film are brought close to each other with the first coating film and the second coating film facing each other. Two coatings were brought into contact.

-8C- Next, in the state where the two coating films are in contact with each other, the two coating films are integrated by heating in an air atmosphere at a temperature of 140 ° C. for 15 minutes to melt, and an average thickness of 50 nm. The light emitting layer was formed.
-9C- Next, an ultraviolet curable resin was supplied by an inkjet method so as to cover the side surface of each formed layer, and then sealed by being cured by ultraviolet irradiation to complete an organic EL element.

(Example 10)
Example 1 except that xylene was supplied onto the intermediate layer after -2A- and the compound (A) contained in the intermediate layer and not bonded to the ITO electrode was dissolved and removed in xylene. In the same manner, an organic EL device was produced.
The average thickness of the intermediate layer from which the compound (A) not bonded to the ITO electrode was removed was 5 nm.

(Comparative Example 1)
[Preparation of intermediate layer forming material]
Compound (I) was dissolved in n-hexadecane to obtain an intermediate layer forming material.
[Production of organic EL element]
Instead of the step-2A-, an intermediate layer having an average thickness of 2 nm is formed by immersing the glass substrate on which the ITO electrode is formed in the intermediate layer forming material previously prepared in an inert atmosphere for 5 minutes. An organic EL device was produced in the same manner as in Example 1 except that.

(Comparative Example 2)
An organic EL device was manufactured after preparing an intermediate layer forming material in the same manner as in Example 1 except that the compound (J) was used as the organic substance.
(Comparative Example 3)
An organic EL device was produced in the same manner as in Example 1 except that Step-2A-, that is, the formation of the intermediate layer was omitted.

2. Evaluation For each of the organic EL elements of the examples and comparative examples, the emission luminance (cd / m ² ) and the maximum emission efficiency (lm / W) were measured, and the time during which the emission luminance was half the initial value (halved) Period).
Moreover, each measured value was calculated | required about five organic EL elements.

The measurement of light emission luminance was performed by applying a voltage of 6 V between the ITO electrode and the AlLi electrode.
And each measured value (luminescence brightness, maximum luminous efficiency, half-life) measured in Comparative Example 3 was used as a reference value, and each measured value measured in each Example and each Comparative Example was divided into the following four stages. Evaluation was performed according to the criteria.

A: The measurement value of Comparative Example 3 is 1.50 times or more. O: The measurement value of Comparative Example 3 is 1.25 times or more and less than 1.50 times. Δ: The measurement value of Comparative Example 3 In contrast, 1.00 times or more and less than 1.25 times x: 0.75 times or more and less than 1.00 times the measured value of Comparative Example 3 Table 1 shows.

As shown in Table 1, each of the organic EL elements of the examples (organic EL elements including a hole transport layer mainly composed of the conductive material of the present invention) is the organic EL elements of Comparative Examples 2 and 3. In comparison with, excellent results were obtained in terms of emission luminance, maximum emission efficiency, and half-life.
As a result, in the organic EL device of the present invention, the adhesion at the interface between the electrode and the intermediate layer is improved, so that it is clear that carriers (holes or electrons) are smoothly injected from the electrode to the intermediate layer. It became.

Further, all of the organic EL elements of each example had excellent results in terms of light emission luminance, maximum light emission efficiency, and half-life as compared with the organic EL element of Comparative Example 1.
Thereby, in the organic EL device of the present invention, holes are prevented from being trapped by silicon atoms contained in the silane coupling agent as in the organic EL device of Comparative Example 1, and therefore, from the electrode to the intermediate layer. It was inferred that the hole injection was smoother.

It is the longitudinal cross-sectional view which showed an example of the organic EL element. It is a longitudinal cross-sectional view which shows embodiment of a display apparatus provided with the organic EL element shown in FIG. 1 is a perspective view showing a configuration of a mobile (or notebook) personal computer to which an electronic apparatus of the present invention is applied. It is a perspective view which shows the structure of the mobile telephone (PHS is also included) to which the electronic device of this invention is applied. It is a perspective view which shows the structure of the digital still camera to which the electronic device of this invention is applied.

Explanation of symbols

  DESCRIPTION OF SYMBOLS 1 ... Organic EL element 2 ... Board | substrate 3 ... Cathode 4 ... Intermediate | middle layer 5 ... Light emitting layer 7 ... Anode 8 ... Sealing member 9 ... Laminated body 100 ... Display apparatus 20 ... Base | substrate 21 ... ... Substrate 22 ... Circuit part 23 ... Protective layer 24 ... Driving TFT 241 ... Semiconductor layer 242 ... Gate insulating layer 243 ... Gate electrode 244 ... Source electrode 245 ... Drain electrode 25 ... First layer Insulating layer 26... Second interlayer insulating layer 27... Wiring 31... First partition 32. Second partition 1100. Mobile phone 1202 …… Operation buttons 1204 …… Earpiece 1206 …… Speaker 1300 …… Digital still camera 1302 …… Case ( Dee) 1304 ...... light receiving unit 1306 ...... shutter button 1308 ...... circuit board 1312 ...... video signal output terminal 1314 input-output terminal 1430 ...... television monitor 1440 ...... personal computer ...... for data communication

Claims (16)

An organic semiconductor layer composed mainly of an organic semiconductor material;
An electrode composed mainly of an inorganic oxide (excluding silicon oxide) at least near the surface;
An intermediate layer that is provided between the organic semiconductor layer and the electrode and is composed mainly of an organic substance having a function of transporting carriers;
For an electronic device, wherein the inorganic oxide and the organic substance are chemically bonded in the vicinity of the interface between the electrode and the intermediate layer, and the chemical bond does not substantially contain a silicon atom. substrate.   2. The electronic device substrate according to claim 1, wherein the organic substance is a compound having a carrier transport part having a function of transporting a carrier and a binding part that couples the carrier transport part and the electrode.   3. The electronic device substrate according to claim 2, wherein among the atoms constituting the bonding portion, the number of the linearly connected atoms is 3 to 10.   The electronic device substrate according to claim 2, wherein the bonding portion includes a hydroxyl group at a terminal thereof.   The electronic device substrate according to claim 1, wherein the chemical bond is an ether bond. The intermediate layer and the organic semiconductor layer are in contact with each other;
The electronic device substrate according to claim 1, wherein the carrier transport portion includes a structure having a high affinity with the organic semiconductor material.   The electronic device substrate according to claim 6, wherein the carrier transporting portion includes an arylamine skeleton. The said organic substance is a board | substrate for electronic devices of Claim 7 which has a compound represented by the following general formula (A1) as a main component.

[Wherein, X ¹ , X ² , X ³ and X ⁴ each independently represent a hydrogen atom, a methyl group, an ethyl group or a substituent represented by the following general formula (B1), May be different. However, at least one of X ¹ , X ² , X ³ and X ⁴ represents a substituent represented by the following general formula (B1), and the other represents a hydrogen atom, a methyl group or an ethyl group. To express. Eight R's each independently represent a hydrogen atom, a methyl group or an ethyl group, which may be the same or different, and Y is a substituted or unsubstituted aromatic hydrocarbon ring, or Represents a group containing at least one substituted or unsubstituted heterocyclic ring. ]

[Wherein n represents an integer of 1 to 8. ] The substrate for electronic devices according to claim 8, wherein each of the substituent X ¹ , the substituent X ² , the substituent X ^3, and the substituent X ⁴ represents a substituent represented by the general formula (B1).   The electronic device substrate according to claim 8 or 9, wherein the group Y includes at least one substituted or unsubstituted aromatic hydrocarbon ring, and is composed of carbon atoms and hydrogen atoms.   The substrate for electronic devices according to claim 8 or 9, wherein the group Y contains at least one substituted or unsubstituted heterocyclic ring.   The electronic device substrate according to claim 1, wherein the intermediate layer has an average thickness of 1 to 50 nm.   The electronic device substrate according to claim 1, wherein the electrode is subjected to a treatment for increasing a surface area thereof.   An electronic device comprising the electronic device substrate according to claim 1.   The electronic device according to claim 14, wherein the electronic device is an organic electroluminescence element.   An electronic apparatus comprising the electronic device according to claim 14.

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