WO2005041318A1 - スイッチング素子 - Google Patents
スイッチング素子 Download PDFInfo
- Publication number
- WO2005041318A1 WO2005041318A1 PCT/JP2004/015519 JP2004015519W WO2005041318A1 WO 2005041318 A1 WO2005041318 A1 WO 2005041318A1 JP 2004015519 W JP2004015519 W JP 2004015519W WO 2005041318 A1 WO2005041318 A1 WO 2005041318A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- switching element
- formula
- compound
- bistable material
- electron
- Prior art date
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- 239000000463 material Substances 0.000 claims abstract description 68
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000000654 additive Substances 0.000 claims abstract description 3
- 230000000996 additive effect Effects 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims description 16
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052737 gold Inorganic materials 0.000 claims description 12
- 239000010931 gold Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- OJPNKYLDSDFUPG-UHFFFAOYSA-N p-quinomethane Chemical compound C=C1C=CC(=O)C=C1 OJPNKYLDSDFUPG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 230000007704 transition Effects 0.000 abstract description 14
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- 239000010410 layer Substances 0.000 description 35
- 238000000034 method Methods 0.000 description 21
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- -1 quinomethane compound Chemical class 0.000 description 15
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- 125000000524 functional group Chemical group 0.000 description 8
- 239000011368 organic material Substances 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- 238000001771 vacuum deposition Methods 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical class NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 description 2
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- APLQAVQJYBLXDR-UHFFFAOYSA-N aluminum quinoline Chemical compound [Al+3].N1=CC=CC2=CC=CC=C12.N1=CC=CC2=CC=CC=C12.N1=CC=CC2=CC=CC=C12 APLQAVQJYBLXDR-UHFFFAOYSA-N 0.000 description 1
- 150000005010 aminoquinolines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
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- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
- H10K10/701—Organic molecular electronic devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/611—Charge transfer complexes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
- H10K10/50—Bistable switching devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
Definitions
- the present invention relates to a switching element for driving an organic EL display panel and a switching element used for a high-density memory or the like, in which an organic bistable material is arranged between two electrodes.
- An organic bistable material is an organic material exhibiting a so-called non-linear response in which when a voltage is applied to a material, the current of a circuit rapidly increases at a certain voltage or more and a switching phenomenon is observed.
- Fig. 5 shows an example of the voltage-current characteristics of the organic bistable material exhibiting the switching behavior as described above.
- the organic bistable material has two current-voltage characteristics, a high resistance characteristic 51 (off state) and a low resistance characteristic 52 (on state).
- Vth2 high transition voltage
- Vthl low transition voltage
- the on state turns off. It has a non-linear response characteristic in which the resistance changes as the state changes. That is, a so-called switching operation can be performed by applying a voltage of Vth2 or more or Vthl or less to this organic bistable material.
- Vthl and Vth2 can be applied as pulsed voltages.
- Adachi et al. Formed a Cu-TCNQ complex thin film using a vacuum deposition method, clarified its switching characteristics, and examined its applicability to an organic EL matrix. Reference 3).
- Non-Patent Document l R.S.Potember et al. Appl.Phys. Lett. 34, (1979) 405
- Non-Patent Document 2 Kumai et al. Solid Physics 35 (2000) 35
- Patent document 3 Proceedings of the Japan Society of Applied Physics Spring 2002 3rd volume 1236
- Patent document 1 International Publication No. 02Z37500 pamphlet
- the current density in the on state is small, and its use has been limited.
- the current density in the on-state of a single-layer structure of an amino-imidazole dicarbo-trilui conjugate which is said to have the highest properties among currently known materials, is high when an IV is applied. And as small as 0. ImAZcm 2 or so.
- the transition voltage from the off state to the on state needs to be higher than the driving voltage of the organic EL, and is at least 5 V or higher.
- the transition voltage from the off state to the on state needs to be higher than the driving voltage of the organic EL, and is at least 5 V or higher.
- the present invention has been made in view of the above-mentioned problems of the related art, and increases the current density in the on state of the switching element to improve the performance as a driving element such as various devices having a high transition voltage. The purpose is to let them.
- the switching element of the present invention is a switching element having two kinds of stable resistance values with respect to a voltage applied between the electrodes, wherein a first electrode layer, an organic bistable material layer, The organic bistable material layer is formed as a thin film in the order of the second electrode layer, and the organic bistable material layer includes a main component composed of an organic bistable material having an electron transporting property and an additive component composed of an electron donating compound.
- an electron-transporting organic bistable material that switches independently is doped with an additional component having an electron-donating property, whereby electrons are converted from an electron-donating compound to an organic compound. It migrates to bistable materials and promotes charge generation in organic materials. Thus, it is considered that the current density can be increased and a high transition voltage can be obtained.
- a switching element using a conventional charge transfer complex generally has a large temperature dependency, and the switching property is exhibited at a low temperature.
- the switching element of the present invention can operate stably from room temperature to around 80 ° C.
- the switching element using the charge transfer complex requires a voltage of about several tens of volts to about 100 volts. According to the present invention, the switching element can operate stably at a voltage of 20 volts or less.
- the organic bistable material having an electron-transporting property is preferably a quinomethane-based compound represented by the following general formula (I). [0018] [Formula 1]
- R 1 to R 4 each represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or a group selected from an aryl group which may have a substituent, R 1 -.
- R 4 may be the same or different R 5
- R 6 represents any good multi heterocycle have an optionally substituted Ariru group or substituent
- R 5 And R 6 may be the same or different
- A represents a group selected from the following (1)-(10).
- the quinomethane-based compound has a quinone group that is an electron-accepting functional group, so that it has an electron-transporting property and has excellent bistable properties. It shows its properties and can be suitably used in the present invention.
- the electron donating compound is a compound represented by the following general formula (II). [0021] [Formula 3]
- R 7 -R 1G represents a hydrogen atom, an alkyl group having 16 carbon atoms which may have a substituent, an aryl group which may have a substituent, Represents a group selected from residues forming a good ring, and R 7 —R 1G may be the same or different.
- the electron donating compound has a large ionization potential of about 6 eV or more and has a high electron donating property, and therefore can be suitably used in the present invention.
- the first electrode layer and Z or the second electrode layer contain gold. According to this aspect, when the organic bistable material is the quinomethane-based compound, particularly excellent switching characteristics are exhibited.
- FIG. 1 is a schematic configuration diagram showing one embodiment of a switching element of the present invention.
- FIG. 2 is a chart showing current-voltage characteristics of a switching element in Example 1.
- FIG. 3 is a chart showing current-voltage characteristics of a switching element in Example 2.
- FIG. 4 is a chart showing current-voltage characteristics of a switching element in Comparative Example 1.
- FIG. 5 is a chart showing the concept of voltage-current characteristics of a conventional switching element.
- Second electrode layer 30 Organic bistable material layer
- FIG. 1 is a schematic configuration diagram showing one embodiment of the switching element of the present invention. As shown in Figure 1, this switching element
- a first electrode layer 21a, an organic bistable material layer 30, and a second electrode layer 21b are sequentially formed as thin films.
- the substrate 10 is not particularly limited, but a conventionally known glass substrate or the like is preferably used.
- the first electrode layer 21a and the second electrode layer 21b include metal materials such as aluminum, gold, silver, chromium, nickel, and iron; Inorganic materials such as conjugated organic materials, organic materials such as liquid crystal, and semiconductor materials such as silicon can be appropriately selected.
- a gold electrode is preferably a gold electrode, and a gold electrode is more preferable.
- the organic bistable material is a quinomethane compound described later, it is particularly preferable to use a gold electrode.
- the electrode containing gold is preferable, but (a) since gold is laminated in a granular manner, the contact state of the interface with the organic film becomes partial, and electrons injected from the counter electrode are injected. Accumulates at the interface, which causes electric field concentration and tunnel injection.
- the (dip) metal diffuses into the organic film to form clusters, and electrons injected from the counter electrode accumulate in the clusters. Tunnel injection occurs due to electric field concentration. Holes are likely to be injected from the (metal) metal into the organic film. Therefore, holes accumulate at the interface between the organic film and the counter electrode, causing electric field concentration and tunnel injection. It can happen.
- the electrode layer 21 As a method for forming the electrode layer 21, a conventionally known method such as a vacuum evaporation method is preferably used, and is not particularly limited.
- the substrate temperature during the deposition is appropriately selected depending on the electrode material used, but is preferably 0 to 150 ° C. Also, the film thickness Pama 50—200mn power preferred! / ⁇ .
- An organic bistable material layer 30 is formed between the two electrode layers 21 as a thin film.
- Methods for forming the organic bistable material layer 30 include a vacuum evaporation method, a spin coating method, an electrolytic polymerization method, a chemical vapor deposition method (CVD method), a monomolecular film accumulation method (LB method), a dip method, and a bar coating method.
- Production methods such as an inkjet method and a screen printing method are used, and there is no particular limitation.
- the substrate temperature during the deposition is appropriately selected depending on the organic bistable material used, but is preferably 0 to 100 ° C.
- the thickness is preferably 20 to 150 nm.
- the coating solvent may be, for example, halogen-based dichloromethane, dichloroethane, chlorophonolem, aethenole-based tetrahydrofuran (THF), or ethylene glycol dimethyl ether.
- THF aethenole-based tetrahydrofuran
- ethylene glycol dimethyl ether ethylene glycol dimethyl ether.
- aromatic toluene, xylene, alcohol-based ethyl alcohol, ester-based ethyl acetate, butyl acetate, ketone-based acetone, MEK, and acetonitrile can be used. Dissolve the organic bistable material in these solvents in the range of 0.001 to 30% by mass, and if necessary, add binder resin to make a coating solution.
- the noinder resin for example, polycarbonate, polyester, polyvinyl alcohol, polystyrene and the like can be used.
- the spin coating conditions can be appropriately set according to the target film thickness, but the rotation speed is preferably in the range of 200 to 3600 rpm.
- the present invention is characterized in that the organic bistable material layer 30 contains a main component composed of an organic bistable material having an electron transporting property and an additional component composed of an electron donating compound.
- an organic bistable material having an electron transporting property has a functional group for transporting charges, and an electron donating functional group and an electron accepting functional group are contained in one molecule. It is preferable to use a compound containing
- Examples of the electron donating functional group include: SCH, -OCH, one NH, one NHCH, and one N (CH).
- fullerene materials such as C are also electron transporting materials. And can be used in the present invention.
- examples of the compound having the above electron donating functional group and the above electron accepting functional group in one molecule include, for example, an aminoimidazole compound, a dicyano compound, and a pyridone.
- Known compounds such as a compound, a styryl compound, a stilbene compound, a quinomethane compound, and a butadiene compound are exemplified.
- R 1 to R 4 each represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or a group selected from an aryl group which may have a substituent, R 1 -.
- R 4 may be the same or different R 5
- R 6 represents any good multi heterocycle have an optionally substituted Ariru group or substituent
- R 5 And R 6 may be the same or different
- A represents a group selected from the following (1)-(10).
- the above quinomethane compound (I) is synthesized, for example, by the following reaction formula. Can.
- A is an example of (2) or (3) (X represents oxygen or sulfur).
- R 7 -R 1G represents a hydrogen atom, an alkyl group having 16 carbon atoms which may have a substituent, an aryl group which may have a substituent, And R 7 —R 1C> may be the same or different.
- Such a compound include a compound represented by the following structural formula (II 1)-(II 11). These are commercially available. For example, as the compounds of the structural formulas (II 1), (II 4) and ( ⁇ -9), those commercially available from Aldrich can be used.
- the optimum amount of the electron-donating compound to be added to the organic bistable material varies depending on each material, but it is controlled so as to be 20% by mass or less based on the whole organic bistable material layer 30. It is preferred to add 0.01 to 20% by mass more preferably 0.05 to 20% by mass is even more preferred 0.5 to 20% by mass is particularly preferred. If the addition amount exceeds 20% by mass, the physical properties of the organic bistable material itself may not be exhibited, which is not preferable.
- the adjustment of the addition amount can be set by adjusting the film forming speed of both.
- the composition can be easily adjusted by forming a film by dissolving both materials in the same solution.
- the current of the organic bistable material in the on state is expressed by the following two equations, based on the charge density N, mobility, permittivity ⁇ , and electron charge e of the material.
- the current having the larger value of the two current modes is observed.
- the space charge limiting current becomes larger than the ohmic current.Therefore, the ohmic current is often observed at a low voltage, and the space charge limiting current is often observed at a high voltage.When the power charge density increases, the voltage of this transition decreases. Due to the rise, ohmic current may be observed in a wide range. In any case, it is important to increase the charge density N and the mobility in order to increase the current density.
- the compound of the above general formula (II) is known as an electron-donating material.
- electrons are converted to the general formula ( ⁇ ) From the compound to the organic bistable material to promote charge generation within the organic material.
- the charge density in the organic bistable material is increased by the above two mechanisms, and the current density is thereby increased.
- a glass substrate is used as the substrate 10, and aluminum is used as the first electrode layer 21a, a quinomethane compound is used as the main component as the bistable material layer 30, and an electron donating material is added thereto by a vacuum evaporation method. Then, a thin film was successively formed of gold as the second electrode layer 21b to form a switching element of Example 1.
- the compound of the above structural formula (I 1) was used as the quinomethane compound, and the compound of the above structural formula (III-1) was used as the electron donating compound.
- the first electrode layer 21a, the organic bistable material layer 30, and the second electrode layer 21b were formed to have a thickness of 100 nm, 80 nm, and 100 nm, respectively. Further, the vapor deposition apparatus in diffusion pumping was performed at a vacuum degree of 3 X 10- 6 torr. Aluminum and gold were deposited by a resistance heating method at a deposition rate of 3 AZsec, and the quinomethane compound and the electron-donating compound were co-evaporated by a resistance heating method. We went at 2AZsec, 0.0AZAZsec. The vapor deposition of each layer was performed continuously by the same vapor deposition apparatus, and was performed under the condition that the sample did not come into contact with air during the vapor deposition.
- a film was formed under the same conditions as in Example 1 except that the quinomethane compound and the electron donating compound were formed at a deposition rate of 2 AZsec and 0.02 AZsec, respectively. Obtained.
- the compound of the above structural formula (I 15) was used as the quinomethane-based compound, and the compound of the above structural formula (9-9) was used as the electron donating compound, and the film formation rate was set at 2 AZsec and 0.03 AZsec, respectively. Otherwise, a film was formed under the same conditions as in Example 1 to obtain a switching element of Example 4.
- a film was formed under the same conditions as in Example 1 except that no electron donating compound was added to the organic bistable material layer 30 to obtain a switching element of Comparative Example 1.
- a switching element of Comparative Example 2 was obtained by forming a film under the same conditions as in Example 3 except that the electron donating compound was not added to the organic bistable material layer 30.
- Table 1 shows the current densities in the on state at the low threshold voltage Vthl, the high threshold voltage Vth2, and the voltage IV, which are the threshold voltages in FIG.
- FIGS. 2-4 show current-voltage characteristics of the switching elements of Examples 1, 2 and Comparative Example 1, respectively.
- the current in the on state is proportional to the square of the voltage
- the current in the embodiment is proportional to the voltage. That is, it can be seen that in the comparative example, the charge density is small and the space charge limited current is used, whereas in the example, the charge density is high and the ohmic current is used.
- Vth2 the voltage at which the transition from the off state to the on state in Example 14 was higher than that of Comparative Examples 1 and 2. It is presumed that the reason for this is that the addition of an electron-donating impurity changes the crystal state of the quinone conjugate and the resulting change in surface shape changes the transition voltage.
- the switching element of the present invention can be suitably used for a switching element for driving an organic EL display panel, a high-density memory, and the like.
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