JP2657564B2 - Schottky diode - Google Patents

Description

Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a Schottky diode formed by bringing a substance forming a Schottky barrier into contact with a specific compound.

[Problems to be Solved by Conventional Technology and Invention] Conventionally, inorganic semiconductor materials such as GaAs and Si have been used for diodes.

In general, a diode requires a semiconductor material of high purity or whose doping concentration is precisely controlled, and this must be processed into a desired shape.

When an inorganic material is used for such a semiconductor, complicated processes such as a zone melt method and a molecular beam epitaxy method are required during the manufacturing process, and processing under extreme conditions such as high vacuum or high temperature is required, and the manufacturing apparatus itself is also large-scale. It will be something. In addition, since it is an inorganic material, there is a problem that the degree of freedom in selecting the material is low.

On the other hand, research on organic semiconductors has been actively conducted in recent years. Among them, conductive polymers have been expected as materials for new electronic devices because they can freely and reversibly control the Fermi level by doping.

As the conductive polymer, a polymer in which a certain compound is doped into a polymer such as polyacetylene, polyparaphenylene, polythiophene, or polypyrrole is known.

However, these conventional conductive polymers have the drawback that they are deteriorated in the air and their electrical characteristics are liable to fluctuate, and they are very difficult to remove impurities or form due to poor solubility and solubility. I have.

Therefore, satisfactory performance could not be obtained even when the conductive polymer was used for a diode.

The present inventors have conducted intensive studies with the aim of solving the above problems, and as a result, a compound obtained by doping an electron acceptor into a specific organic compound can be used as a p-type region of a Schottky diode, and The present inventors have found that a Schottky diode exhibits sufficient performance, and have reached the present invention.

[Means for Solving the Problems] That is, the present invention provides a Schottky diode characterized in that a compound obtained by doping an electron acceptor into a compound represented by the following general formula (1) is used as a p-type region. To provide.

(Wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ each represent hydrogen or a hydrocarbon residue having 1 to 20 carbon atoms, which may be the same or different, and Ar ¹ and Ar ² are each Represents a divalent aromatic hydrocarbon residue, 1 is 0 or more, m is 1 or more, and n is 2
Hereinafter, the present invention will be described in detail.

The Schottky diode of the present invention is characterized in that a compound obtained by doping the compound represented by the general formula (1) with an electron acceptor (hereinafter, referred to as compound (A)) is used as a p-type region. And a metal (hereinafter, referred to as metal (B)).

The Schottky diode mentioned here is a diode having a rectifying function, which is obtained by joining a certain metal to a p-type semiconductor.

Further, the p-type region here is a region of the p-type semiconductor occupying in the Schottky diode.

The compound (A) used in the present invention is obtained by doping the compound represented by the general formula (1) with an electron acceptor.

In the compound represented by the general formula (1), R ¹ , R ² ,
R ³ , R ⁴ and R ⁵ each represent hydrogen or a hydrocarbon residue having 1 to 20, preferably 1 to 12 carbon atoms. R ¹ ,
R ² , R ³ , R ⁴ and R ⁵ may be the same or different from each other.

Specifically, as R ¹ , for example, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group,
Alkyl groups such as i-butyl group and n-hexyl group; hydrocarbon groups exemplified by alkoxy groups such as methoxy group and ethoxy group and derivatives thereof; and hydrogen, preferably methyl group and ethyl group , A methoxy group and an ethoxy group are preferred. As R ² and R ³ , for example, a methyl group,
An alkyl group such as an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, and an n-hexyl group;
Also, a hydrocarbon residue or hydrogen represented by an alkoxyphenyl group such as a methoxyphenyl group or an ethoxyphenyl group, an alkylphenyl such as a tolyl group or an ethylphenyl group, various aryl groups such as a phenyl group, an aralkyl group, and derivatives thereof. And preferably a methyl group, an ethyl group, an i-propyl group, an n-propyl group, a tolyl group, an ethylphenyl group and hydrogen.

R ⁴ and R ⁵ include, for example, alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, n-hexyl group, methoxyphenyl group, ethoxy group and the like. Alkoxyphenyl group such as phenyl group, tolyl group, alkylphenyl group such as ethylphenyl group, phenyl group, chlorophenyl group, various aryl groups such as nitrophenyl group, aralkyl group and derivatives thereof,
Examples include a hydrocarbon residue or hydrogen exemplified by a furyl group, a pyridine group and the like, and preferably a methyl group, an ethyl group, i
-Propyl, n-propyl, phenyl, tolyl and hydrogen are preferred.

Further, A in the compound represented by the general formula (1)
r ¹ and Ar ² represent a divalent aromatic hydrocarbon residue, and Ar ¹ and Ar ² may be the same or different. Specifically, as Ar ¹ , general formulas (2), (3) and (4): (Wherein R ¹ is the same as in the general formula (1)), for example, a p-phenylene group, an m-phenylene group, a p-biphenylene group, a methyl-p-phenylene group, an ethyl-p-phenylene group And various phenylene groups such as methoxy-p-phenylene group, methyl-m-phenylene group, ethyl-m-phenylene group, and methoxy-m-phenylene group, and derivatives thereof.

Further, as Ar ² , for example, the general formulas (2) and (3)
In addition to various phenylene groups and derivatives thereof represented by (4) and 1,5- or 2,7-naphthylene group, 1,4
-, 1,5- or 2,6-anthraquinonylene group, 2,4- or 2,7-fluorenonylene group, 2,7-fluorenylene group, birenylene group, 2,7-phenanthraquinonylene group,
2,7- (9-dicyanomethylene) fluorenonylene group,
A divalent monocyclic or condensed polycyclic aromatic hydrocarbon residue exemplified by a dibenzotrobondiyl group, a dicyanomethylenedibenzotrobondiyl group, a benzanthronylene group, etc., and a 2-phenylbenzoxazolediyl group , 2
-Phenylbenzimidazolediyl group, carbazolediyl group, 2-phenylbenzothiazoldiyl group, 2
Divalent groups exemplified by divalent heterocyclic groups such as -phenylbenzotriazolediyl group, dibenzothiophenediyl group, dibenzothiophenoxide diyl group, 9-acridonediyl group, xanthonediyl group and phenoxazinediyl group; And heteroatom-containing condensed heterocyclic aromatic hydrocarbon residues.

l is an integer of 0 or more, usually 0 to 50, preferably 0
To 10, more preferably 0 to 5. m is 1 or more and is usually 1 to 50, preferably 1 to 30. n is 2 or more,
Usually 2 to 1000, preferably 5 to 500, more preferably 2
0 to 200, having a substantially linear structure.
Although both terminals of the formula (1) are not particularly specified, they are usually nuclear-substituted hydrogen.

When l = 0 and m = 1, in order to further enhance the effect of the present invention, n is more than 20, preferably 30 to 1,000, and more preferably 40 to 200. desirable.

The compound represented by the general formula (1) is usually produced by polycondensing the compound represented by the general formula (5) with the compound represented by the general formula (6) or a polymer thereof. The production method is not limited at all.

R ⁴ COR ⁵ (6) (wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and Ar ¹ , Ar ^{2 and} l, m
Is the same as in the general formula (1). As the compound represented by the general formula (5), N, N'-
Diphenyl-p-phenylenediamine compound, N-phenyl-N '-(4-phenylamino) phenyl-p-
Examples include phenylenediamine-based compounds.

Of the compounds represented by the general formula (5), those having m of 2 or more are usually prepared by using an oxidizing agent such as a manganese compound or a ferric salt when m = 1 represented by the general formula (5). It is manufactured by using a method such as an oxidative coupling reaction or electrolytic oxidative polymerization. For example, when the compound represented by the general formula (5) is N, N'-diphenyl-p-
In the case of a phenylenediamine compound, N, N'-diphenyl-p-phenylenediamine is converted to ethanol, acetone,
It can be produced by an oxidative coupling reaction in a solvent such as acetonitrile, ether, benzene or the like, using ferric chloride as a catalyst.

The reaction temperature at this time is from −50 ° C. to 100 ° C., preferably from −20 ° C. to the boiling point of the solvent used, and the reaction time can be from 10 minutes to 100 hours, preferably from 1 hour to 50 hours.

Note that among these N, N'-diphenyl-p-phenylenediamine-based compounds, typical ones are N, N '
-Dimethyl-N, N'-diphenyl-p-phenylenediamine, N, N'-diethyl-N, N'-diphenyl-p-phenylenediamine, N, N'-dipropyl-N, N'-diphenyl-p- Examples include phenylenediamine.

Examples of the compound represented by the general formula (6) include various carbonyl compounds such as aldehydes, aldehyde polymers, and ketones.

Representative aldehydes include formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, benzaldehyde, acrylaldehyde, cinnamaldehyde, anisaldehyde, nicotinaldehyde, nitrobenzaldehyde, chlorobenzaldehyde, furfural and the like.

Further, the aldehyde polymer refers to a concentrated solution of the aldehyde represented by the general formula (6) and self-condensation,
Represents a polymer obtained by condensation in the presence of an acid catalyst,
The polymer is one which easily hydrolyzes under the reaction conditions for synthesizing the copolymer of the present invention to produce an aldehyde monomer. Representative examples include paraformaldehyde, which is a polymer of formaldehyde, and paraaldehyde, which is a trimer of acetaldehyde.

Examples of the ketone include acetone, ethyl methyl ketone, diethyl ketone, cyclohexyl acetone, and the like.

The polycondensation of the compound represented by the general formula (5) and the compound represented by the general formula (6) can be carried out in an organic solvent in which both are soluble at a temperature of 0 to 200 ° C. using an acid or alkali catalyst. it can. Examples of acid catalysts are sulfuric acid, hydrochloric acid, phosphoric acid, perchloric acid, inorganic acids such as diphosphorus pentoxide, formic acid, acetic acid,
Organic acids such as propionic acid, methanesulfonic acid and p-toluenesulfonic acid can be mentioned. These acid catalysts may be used alone or in combination of two or more. Examples of preferred organic solvents include ethers such as ethyl ether, tetrahydrofuran and dioxane, halogenated hydrocarbons such as chloroform, dichloromethane and chlorobenzene, nitro compounds such as nitrobenzene, acetonitrile, propylene carbonate, dimethylformamide, and N-methyl. And pyrrolidone. The reaction time can be appropriately selected within the range of 1 minute to 500 hours, preferably 5 minutes to 200 hours.

The compound represented by the general formula (1) thus obtained is usually soluble in organic solvents such as chloroform, benzene, tetrahydrofuran (THF), CH ₂ Cl ₂ , N-methylhydrin, nitrobenzene, etc. It can be molded.

Since the compound represented by the general formula (1) is soluble as described above, impurities can be usually removed by purification or the like for the purpose of further improving the performance and the like. Examples thereof include GPC (Gel permeation Chromatography), chromatography on ion exchange resins, etc., reprecipitation method and washing method using an insoluble solvent such as ethanol and hexane, and extraction method using the above-mentioned soluble solvent.

The compound (A) of the present invention is obtained by doping the compound represented by the general formula (1) with an electron acceptor.

Known doping methods can be used, for example, a chemical method of directly adding an electron acceptor, an electrochemical method of performing electrolytic oxidation in a solvent containing an anion serving as an electron acceptor, and an electron acceptor. Any method such as an ion implantation method in which ions are accelerated and implanted into a substance can be used.

The electron acceptor used in the present invention is not particularly limited as long as the object of the present invention is not impaired.

Among the electron acceptors, those specifically used for doping by a chemical method include, for example, iodine, bromine, halogen compounds such as hydrogen iodide, arsenic pentafluoride, phosphorus pentafluoride, phosphorus pentachloride, Metal halides such as antimony pentafluoride, silicon tetrafluoride, aluminum chloride, aluminum bromide, aluminum fluoride, ferric chloride,
Examples thereof include protonic acids such as sulfuric acid, nitric acid and chlorosulfonic acid, oxidizing agents such as sulfur trioxide and difluorosulfonyl peroxide, and organic substances such as tetracyanodimethane.

Further, as the electron acceptor capable of electrochemically doped, for example, _{^{PF 6 -, SbF 6 -,}} As 6 - Va metal selected halide anions, such as, BF ₄ ^- halogen Group IIIa elements, such as compound _{^{anion, I - (I 8 -)}} , Br -, Cl - halogen anion such as, ClO ₄ ^- include anions such perchlorate anions such as.

Further, electron acceptors that can be doped by ion implantation include, for example, Br ⁺ , Cl ⁺ , and I ⁺ .

The doping concentration is usually preferably 0.001 mol or more per unit of the repeating unit represented by the general formula (1).

In the present invention, the compound (A) thus obtained is used as a p-type region of a Schottky diode, and the compound (A) and the metal (B) are joined to form a Schottky junction. Thus, a Schottky diode is obtained.

In the present invention, the compound (A) and the metal (B) are brought into contact with each other at least on one or all of their surfaces, and this portion is made into a Schottky junction. However, at this time, at least one or more surfaces of the compound (A) are left without bonding to the metal (B).

Here, the work function of the metal (B) is the compound (A)
Any metal may be used as long as it has a work function smaller than the above and does not chemically react with the compound (A).

That is, for example, Al, In, W, Ti, Mo, and the like are suitable as the metal (B), and Al, In, or the like is preferably used.

Further, as a joining method of the compound (A) and the metal (B), a method of vacuum-depositing the metal (B) on the molded compound (A), a method of dipping the compound (A) on the metal (B), and a method of casting And a method of forming at the same time as joining by a spin coating method. Preferably, a vacuum evaporation method is used.

At this time, the shape, area, thickness, and the like of the metal (B) can be appropriately selected depending on the purpose, and are not particularly limited.

In addition, when a vacuum deposition method is used, the temperature at the time of bonding can be appropriately selected as long as the temperature of the compound (A) is usually 400 ° C. or lower, and a solvent is used by a dipping method, a casting method, a spin coating method, or the like. When the solvent is further removed, it can be appropriately selected as long as it is usually higher than the freezing point of the solvent and lower than the boiling point of the solvent, and can be usually performed at -20 to 400 ° C.

At this time, it is preferable that the bonding be performed under an inert atmosphere.

When joining the above compound (A) and metal (B),
The doping can also be performed before doping, that is, after bonding the compound represented by the general formula (1) and the metal (B).

The Schottky diode of the present invention is obtained by joining the above compound (A) and metal (B),
A method for using the Schottky diode for an element will be described.

In order to use the Schottky diode as an element, an electrode (C) is provided on a portion of the compound (A) that is not bonded to the metal (B) so as not to make direct contact with the metal (B).

The method for using the Schottky diode of the present invention in an element includes a step of doping, a step of molding the compound represented by the general formula (1) or the compound (A) (hereinafter, referred to as a molding step), A step of joining the compound or compound (A) represented by (1) to the metal (B) (hereinafter referred to as a step of joining the metal (B)), and a step of joining the compound or compound (A) represented by the general formula (1) to an electrode Each step of the step of joining with (C) (hereinafter, the step of joining the electrode (C)) is included.

The order of the above steps is not usually limited and can be determined according to the method selected in each step.

First, the method of the doping step is as described above.

 Next, the method of the molding step will be described.

The shape of the Schottky diode element obtained in the present invention is not particularly limited. In particular, the compound represented by the general formula (1) and the compound (A) have a feature of being soluble in a solvent as described above, and therefore, any shape can be selected.

For example, a thin film shape, a roll shape, a shape incorporated in another element, and the like can be mentioned, but it is preferable to have two or more surfaces.

When used in the form of a thin film, the thickness can be appropriately determined according to the purpose. Usually, it is desirable to be 5 μm or less, preferably 0.01 to 3 μm.

The forming method is not particularly limited. For example, the film can be formed into a thin film by a dipping method, a casting method, a spin coating method, or the like, or can be formed into a roll by winding the film.

In the case of performing the above-mentioned molding, the molding and the evaporation of the solvent can be performed at a temperature higher than the freezing point of the solvent, and within a temperature range lower than the boiling point of the solvent. Can be performed at 400 ° C.

Next, a bonding step of the metal (B) will be described. As the metal (B), those described above are used.

Compound or compound (A) represented by general formula (1)
And the metal (B) are joined on all or at least one surface of each other. However, at this time, it is necessary to leave at least one surface of the compound represented by the general formula (1) or the compound (A) without bonding to the metal (B).

Compound or compound (A) represented by general formula (1)
The method of joining the metal (B) to
And the metal (B) can be used.

Further, the bonding step of the electrode (C) will be described below.
The electrode (C) is bonded to the compound represented by the general formula (1) or the compound (A) on all or a part of at least one surface of each other. At this time, do not directly connect to the metal (B).

At this time, the material of the electrode (C) is selected so as to form an ohmic junction between the compound (A) and the electrode (C),
Therefore, any material having a work function higher than that of the compound (A) can be used for the electrode (C).

As a material of the electrode (C) satisfying this, for example, Au, P
t, ITO (Indium Tin Oxide) and the like are used, and particularly, Au, Pt and the like are preferably used.

The method of joining the compound or compound (A) represented by the general formula (1) and the electrode (C) includes a method of bonding the electrode (C) on the molded compound or the compound (A) represented by the general formula (1). In which the compound represented by the general formula (1) or the compound (A) is formed on the electrode (C) by dipping, casting, or spin coating simultaneously with joining.

At this time, the shape, area, thickness and the like of the electrode (C) can be appropriately selected according to the purpose, and are not particularly limited.

In addition, when a vacuum deposition method is used, the temperature at the time of bonding can be appropriately selected as long as the temperature of the compound represented by the general formula (1) or the compound (A) is usually 400 ° C. or lower.
When a solvent is used in a dipping method, a casting method, a spin code method, or the like, and the solvent is further removed, the temperature can be appropriately selected as long as the temperature is higher than the freezing point of the solvent and lower than the boiling point of the solvent, and is usually -20 to 400. C. can be performed.

At this time, it is preferable that the bonding be performed under an inert atmosphere.

The order in which the above-described doping step, forming step, metal (B) bonding step, and electrode (C) bonding step are performed can be freely selected as appropriate according to the method of each step.

For example, when joining the metal (B) by a vacuum deposition method, first, a forming step is performed, then the metal (B) is vacuum-deposited and doped, and the electrode (C) is joined by vacuum deposition, or A method in which the compound represented by the general formula (1) is formed on (C) by a casting method, joined, doped, and then vacuum-deposited with the metal (B).

When the electrode (C) is joined by a vacuum deposition method,
The method described above, or a method of molding, joining, and doping the compound represented by the general formula (1) on the metal (B) by casting, and then vacuum-depositing the electrode (C), and the like.

[Effect of the Invention] Since the Schottky diode of the present invention uses a specific compound soluble in a solvent in its p-type region, it has good workability and can select a free shape. In addition, since large-area devices can be manufactured with high accuracy using the above properties, they are also useful in the field of giant microelectronics.

EXAMPLES Hereinafter, the present invention will be described specifically with reference to Examples, but the present invention is not limited thereto.

Example 1 N, N'-dimethyl-N, N'-diphenyl-p-phenylenediamine 1.0 was placed in a 100 ml three-necked flask purged with nitrogen.
g, 15 ml of nitrobenzene and 6 ml of acetic acid were added and dissolved, and 120 μl of sulfuric acid and 250 μl of propionaldehyde were added and reacted at 50 ° C. with stirring for 140 hours. The reaction solution was poured into 300 ml of ethanol containing an aqueous solution of 30 ml of 1N-NaOH, the off-white precipitate was filtered, washed with ethanol and distilled water, and dried to obtain 0.85 g of off-white powder. ¹ H-NMR, ¹³ C-NMR and IR (FIG. 1) of the obtained powder were measured, and N, N′-dimethyl-N, N′-diphenyl-p-phenylenediamine propionaldehyde having the following structure was obtained. It was found to be a condensation polymer (degree of polymerization: about 20).

_{^{1 H-NMR (C 6 D}} 6) :( ppm) 6.82~7.20 (m), 3.65
(M), 2.97 (m), 2.02 (m), 0.92 (t) ¹³ C-NMR (CDCl ₃ ): (ppm) 147.4, 143.7, 137.4, 128.4, 1
22,6,118.6,51.8,40.4,28.9,12.9 Next, gold vapor deposition was performed on the glass substrate to a thickness of 2000 mm.
The above N, N'-dimethyl-N, N'-diphenyl-p-phenylenediamine propionaldehyde condensed polymer dissolved in chloroform (concentration: 5 mg / m 2)
l) is dip-coated to form a thin film with a thickness of about 0.3μm,
After drying at room temperature for 20 hours in a nitrogen atmosphere, iodine was doped. The iodine doping was carried out by leaving at room temperature for 10 minutes in a sealed container containing iodine powder.

In addition, aluminum is deposited (film thickness: 3000 mm)
A Schottky diode device was obtained (FIG. 2).

When the voltage-current characteristics (room temperature) of the diode thus obtained were measured, a good rectifying action was exhibited (FIG. 3).

Comparative Example 1 A chloroform solution (concentration: 5 mg / ml) of the N, N'-dimethyl-N, N'-diphenyl-p-phenylenediaminepropionaldehyde polycondensate prepared in Example 1 was applied to a gold-deposited glass substrate. Dip coat to a thickness of about 0.4μ
After drying at room temperature under a nitrogen atmosphere for 20 hours, aluminum was deposited without iodine doping (thickness: 3000 °). When this voltage-current characteristic was measured by the same method as in Example 1, no rectifying action was exhibited (FIG. 4).

Example 2 2.5 g of N, -tolyldiphenylamine was added to a 100-ml three-necked flask purged with nitrogen, and 20 ml of nitrobenzene was added to dissolve the mixture. I let it. The reaction solution was poured into 300 ml of ethanol, and an off-white precipitate was filtered.
After washing with ethanol and distilled water, it was further purified by reprecipitation with a chloroform-ethanol system and dried to obtain 2.6 g of a white powder. As a result of GPC measurement of the obtained powder, a polymer having a peak top molecular weight of about 9000 (degree of polymerization of about 31) in the elution curve was obtained. In addition, ¹ H-NMR, ¹³ C-NMR (FIG. 5) and IR measurement revealed that it was an N-tolyldiphenylamine-paraaldehyde condensation polymer having the following structure.

Next, gold vapor deposition was performed on the glass substrate to a thickness of 2000 mm.
N-tolyldiphenylamine-paraaldehyde polycondensate dissolved in chloroform (concentration: 5 mg)
/ ml) was dip-coated to form a thin film having a thickness of about 0.3 µm, dried under a nitrogen atmosphere at room temperature for 20 hours, and doped with iodine in the same manner as in Example 1. Further, a Schottky diode device was obtained by evaporating aluminum (film thickness: 3000 °).

When the voltage-current characteristics of the diode thus obtained were measured in the same manner as in Example 1, a good rectifying action was exhibited.

Example 3 N, N'-dimethyl-N, N'-diphenyl-p-phenylenediamine 1.0 was placed in a 100 ml three-necked flask purged with nitrogen.
g, dissolve by adding 15 ml of nitrobenzene,
Add 80 μl of Eaton reagent and 1.5 ml of paraaldehyde to add
The reaction was performed at 4 ° C. for 4 hours. The reaction solution was poured into 300 ml of ethanol containing a 30 ml aqueous solution of 1N-NaOH, and an off-white precipitate was filtered, washed with ethanol and deposition water, and then dried to obtain 0.95 g.
Off-white powder was obtained. ¹ H-NMR, ¹³ C-NM of the obtained powder
When measured for R and IR (Fig. 6), it has the following structure
It was found to be a condensation polymer of N, N'-dimethyl-N, N'-diphenyl-p-phenylenediamine-paraaldehyde (degree of polymerization: about 50).

Next, gold vapor deposition was performed on the glass substrate to a thickness of 2000 mm.
On the gold-deposited surface, N, N'-dimethyl-N, N'-diphenylparaphenylenediamine dissolved in chloroform
Dip-coated with a paraaldehyde polycondensate (concentration: 5 mg / ml) to form a thin film of about 0.4 μm under nitrogen atmosphere.
After drying at room temperature for 20 hours, bromine was doped. Bromine doping is performed at room temperature in a sealed container with bromine liquid.
Performed by allowing to stand for 10 minutes. Further, aluminum was deposited (film thickness: 3000 Å) to obtain a Schottky diode device.

When the voltage-current characteristics of the diode thus obtained were measured in the same manner as in Example 1, a good rectifying action was exhibited.

Example 4 A chloroform solution (concentration: 5 mg / ml) of the N, N'-dimethyl-N, N'-diphenylparaphenylenediamine-paraaldehyde polycondensate prepared in Example 3 was gold-deposited on a glass substrate. Dip coat on the evaporation surface, thickness about 0.
After forming a thin film of 4 μm and drying at room temperature for 20 hours in a nitrogen atmosphere, iodine was doped in the same manner as in Example 1. Further, a device of a Schottky diode was obtained by evaporating indium (film thickness: 3000 Å).

When the voltage-current characteristics of the diode thus obtained were measured in the same manner as in Example 1, a good rectifying action was exhibited.

[Brief description of the drawings]

FIG. 1 is an IR chart (infrared absorption spectrum) of the condensation polymer obtained in Example 1, FIG. 2 is a cross-sectional view of the Schottky diode element obtained in Example 1, and FIG. Is a graph showing the voltage-current characteristics of the Schottky diode element obtained in Example 1, FIG. 4 is a graph showing the voltage-current characteristics of the Schottky diode element obtained in Comparative Example 1, and FIG. Is a chart of ¹³ C-NMR of the condensed polymer obtained in Example 2, and FIG. 6 is an IR chart (infrared absorption spectrum diagram) of the condensed polymer obtained in Example 3. 1 ... aluminum deposition layer, 2 ... ioso-doped N, N'-
Dimethyl-N, N'-diphenyl-P-phenylenediamine propionaldehyde polycondensate, 3 ... gold deposited layer, 4 ...
Glass substrate.

Claims (2)

(57) [Claims] 1. The general formula (1) (Wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ each represent hydrogen or a hydrocarbon residue having 1 to 20 carbon atoms, which may be the same or different, and Ar ¹ and Ar ² are each Represents a divalent aromatic hydrocarbon residue, 1 is 0 or more, m is 1 or more, and n is 2
A Schottky diode characterized in that a compound obtained by doping an electron acceptor into a compound represented by the following formula is used as a p-type region. (A) General formula (1) (Wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ each represent hydrogen or a hydrocarbon residue having 1 to 20 carbon atoms, which may be the same or different, and Ar ¹ and Ar ² are each Represents a divalent aromatic hydrocarbon residue, 1 is 0 or more, m is 1 or more, and n is 2
A compound obtained by doping an electron acceptor with a compound represented by the following formula: Characteristic Schottky diode.