WO2002052581A1 - Film fin organique conducteur et son procede de fabrication, dispositif photoelectrique organique, fil electrique et electrode mettant en oeuvre ledit film - Google Patents
Film fin organique conducteur et son procede de fabrication, dispositif photoelectrique organique, fil electrique et electrode mettant en oeuvre ledit film Download PDFInfo
- Publication number
- WO2002052581A1 WO2002052581A1 PCT/JP2001/011324 JP0111324W WO02052581A1 WO 2002052581 A1 WO2002052581 A1 WO 2002052581A1 JP 0111324 W JP0111324 W JP 0111324W WO 02052581 A1 WO02052581 A1 WO 02052581A1
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- WO
- WIPO (PCT)
- Prior art keywords
- group
- conductive
- thin film
- organic thin
- organic
- Prior art date
Links
- 239000010409 thin film Substances 0.000 title claims abstract description 115
- 238000000034 method Methods 0.000 title claims description 94
- 230000008569 process Effects 0.000 title description 16
- 239000000758 substrate Substances 0.000 claims abstract description 72
- 125000000524 functional group Chemical group 0.000 claims abstract description 49
- 125000005647 linker group Chemical group 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 239000010408 film Substances 0.000 claims description 170
- 238000006116 polymerization reaction Methods 0.000 claims description 96
- 239000002356 single layer Substances 0.000 claims description 49
- 238000004519 manufacturing process Methods 0.000 claims description 36
- 239000010410 layer Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 230000005693 optoelectronics Effects 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000009825 accumulation Methods 0.000 claims description 18
- 230000003197 catalytic effect Effects 0.000 claims description 15
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 15
- 230000003647 oxidation Effects 0.000 claims description 15
- 238000007254 oxidation reaction Methods 0.000 claims description 15
- 239000011521 glass Substances 0.000 claims description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 9
- 229920000128 polypyrrole Polymers 0.000 claims description 9
- -1 polychenylene Polymers 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000010894 electron beam technology Methods 0.000 claims description 7
- 229920003026 Acene Polymers 0.000 claims description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 238000003379 elimination reaction Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229920001197 polyacetylene Polymers 0.000 claims description 5
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 4
- 238000003795 desorption Methods 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 229920000015 polydiacetylene Polymers 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 238000010908 decantation Methods 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 239000004020 conductor Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000001186 cumulative effect Effects 0.000 description 32
- 230000008859 change Effects 0.000 description 20
- 238000004132 cross linking Methods 0.000 description 19
- 238000010586 diagram Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 239000004973 liquid crystal related substance Substances 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 230000005684 electric field Effects 0.000 description 7
- 239000003365 glass fiber Substances 0.000 description 7
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- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 210000002858 crystal cell Anatomy 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 2
- 229910018540 Si C Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
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- 239000011247 coating layer Substances 0.000 description 2
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- 238000000151 deposition Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 238000007699 photoisomerization reaction Methods 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
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- 229920006254 polymer film Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 241001619461 Poria <basidiomycete fungus> Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000007697 cis-trans-isomerization reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 230000001590 oxidative effect Effects 0.000 description 1
- 239000011941 photocatalyst Substances 0.000 description 1
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- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
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Classifications
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- 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 potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133719—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films with coupling agent molecules, e.g. silane
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/125—Intrinsically conductive polymers comprising aliphatic main chains, e.g. polyactylenes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
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- 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 potential barriers
- H10K10/701—Organic molecular electronic devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/60—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation in which radiation controls flow of current through the devices, e.g. photoresistors
- H10K30/65—Light-sensitive field-effect devices, e.g. phototransistors
-
- 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
- H10K85/701—Langmuir Blodgett films
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/02—Alignment layer characterised by chemical composition
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/02—Alignment layer characterised by chemical composition
- C09K2323/023—Organic silicon compound, e.g. organosilicon
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133784—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by rubbing
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133796—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers having conducting property
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F2202/00—Materials and properties
- G02F2202/02—Materials and properties organic material
- G02F2202/027—Langmuir-Blodgett film
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- 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 potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/191—Deposition of organic active material characterised by provisions for the orientation or alignment of the layer to be deposited
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/91—Product with molecular orientation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Definitions
- the present invention relates to a conductive organic thin film using an organic material and a method for producing the same, and an organic optoelectronic device, an electric wire, and an electrode using the same. More specifically, the present invention relates to a monomolecular film or a monomolecular accumulation film having conductivity and photoresponsiveness, or an organic optoelectronic device utilizing electric changes of a thin film, and an electric wire and an electrode.
- the Applicant has polyacetylene in at to, polydiacetylene, polyacene (PoIy acene), polyphenylene Eniren, Poriche two Ren, polypyrrole, proposes a conductive film including conductive conjugated groups, such as Poria diphosphate (JP 2 (1990) -27766, USP 5,008,127, EP-A-0385656, EP-A-0339677, EP-A-0552637, USP 5,270,417 ) -242352 No.).
- conductive conjugated groups such as Poria diphosphate (JP 2 (1990) -27766, USP 5,008,127, EP-A-0385656, EP-A-0339677, EP-A-0552637, USP 5,270,417 ) -242352 No.
- organic electronic devices are disclosed, for example, in Japanese Patent Nos. 2034197 and 2507153.
- the organic electronic devices described in these publications are organic electronic devices that switch a current flowing between terminals in response to an applied electric field.
- the conventional organic conductive film has a problem that its conductivity is lower than that of metal. There was a title.
- crystal defects have become a problem as the miniaturization has progressed, and there has been a problem that the deposition performance is greatly affected by the crystals. There was also the problem of poor flexibility.
- the present invention has been made in view of the above, and an object of the present invention is to fabricate a device using an organic substance that is not affected by crystallinity even if the density of the device is increased and fine processing of 0.1 im or less is performed. Accordingly, it is an object of the present invention to provide a highly integrated conductive and photoresponsive device. Another object of the present invention is to provide an organic optoelectronic device having excellent flexibility by being formed on a plastic substrate or the like.
- the conductive organic thin film of the present invention is characterized in that one end of an organic molecule is covalently bonded to the surface of a base material, and a terminal binding group is present in any part of the organic molecule.
- a conjugated bonding group polymerized with another molecule; and a light-responsive functional group containing no active hydrogen in any portion between the terminal bonding group and the conjugated bonding group.
- the conjugated bonding group is polymerized with a conjugated bonding group of another molecule to form a conductive network.
- the method for producing a conductive organic thin film comprises the steps of: providing one end of an organic molecule with a terminal functional group capable of covalently bonding to a substrate surface; A compound comprising a molecule containing a photoresponsive functional group containing no active hydrogen in any portion between the terminal binding group and the conjugated binding group, An organic thin film that forms a covalent bond by a elimination reaction is formed by bringing the organic thin film into contact with a substrate having active hydrogen or to which active hydrogen has been added, and the organic molecules constituting the organic thin film are oriented in a predetermined direction. Tilted and oriented, electrolytic oxidation polymerization of the conjugated groups, catalyst A step of forming a conductive network by conjugate bonding by at least one polymerization method selected from polymerization and energy beam irradiation polymerization.
- the two-terminal organic optoelectronic device of the present invention includes: a first electrode formed on a substrate; a second electrode separated from the first electrode; and the first electrode and the second electrode.
- a two-terminal organic optoelectronic device comprising: a conductive organic thin film that is electrically connected; wherein the conductive organic thin film has a terminal binding group in which one end of an organic molecule is covalently bonded to a substrate surface; A photo-response that does not contain active hydrogen in any part of the organic molecule and between the terminal bonding group and the conjugate bonding group, which is a conjugate bonding group polymerized with another molecule; It is characterized in that the organic molecule includes a functional group, the organic molecule is oriented, and the conjugated group is polymerized to form a conductive network.
- an electric cable according to the present invention is an electric cable comprising: a core wire; a conductive organic thin film formed in a length direction of the core wire surface; and an insulating coating covering the conductive organic thin film.
- the conductive organic thin film includes a terminal bonding group in which one end of an organic molecule is covalently bonded to a substrate surface of a core wire, and a conjugate bonding group present in any part of the organic molecule and polymerized with another molecule.
- a photoresponsive functional group containing no active hydrogen in any part between the terminal binding group and the conjugated binding group, the organic molecule is oriented, and the conjugated group is Is characterized by forming a conductive network by polymerization by electrolytic oxidation polymerization.
- the electrode of the present invention is a transparent electrode at a light wavelength in a visible light region, wherein the electrode has an end-bonding group in which one end of an organic molecule is covalently bonded to a substrate surface; A photo-responsive functional group that does not contain active hydrogen is present in any portion between the terminal binding group and the conjugated binding group that is present in the portion and is polymerized with another molecule.
- the organic molecules are oriented
- the conjugated bonding group is a conductive organic thin film polymerized to form a conductive network.
- FIG. 1A is a conceptual cross-sectional view in which a conductive monolayer formed on a substrate according to Embodiment 1 of the present invention is enlarged to a molecular level
- FIG. 1B is a plan view thereof.
- FIG. 2 is a conceptual diagram for explaining a rubbing alignment method according to Embodiment 1 of the present invention.
- FIG. 3 is a conceptual diagram for explaining a photo-alignment method according to the first embodiment of the present invention.
- FIG. 4 is a conceptual diagram for explaining the pulling orientation method according to the first embodiment of the present invention.
- FIGS. 5A to 5D are conceptual diagrams of a monomolecular cumulative film according to Embodiment 2 of the present invention, which are enlarged to the molecular level, showing a structural example.
- FIG. 5A shows a cumulative film using a chemisorption method.
- FIG. 5B is a cross-sectional view of an X-type conductive monomolecular cumulative film in which the orientation directions of the molecular layers are the same, and
- FIG. 5B is a cumulative film in which the second and subsequent layers are formed using the Langmuir-Blodgett method.
- Fig. 5C is a cross-sectional view of a Y-type conductive monomolecular cumulative film in which the orientation direction of each monolayer is the same direction, and Fig.
- FIG. 5C is a cross-sectional view of an X-type conductive monomolecular cumulative film in which the orientation direction differs for each monolayer.
- FIG. 5D is a cross-sectional view of an X-type conductive monomolecular accumulation film oriented in one of two orientation directions for each monolayer.
- FIGS. 6A and 6B are conceptual diagrams in which the structure of the two-terminal organic optoelectronic device according to Embodiment 3 of the present invention is enlarged to the molecular level.
- FIG. 6A shows first and second electrodes formed on the substrate surface.
- FIG. 6B is a cross-sectional view of the structure in which the first and second electrodes are formed on the surface of the organic thin film.
- FIG. 7A and 7B show two terminals for light irradiation according to the third embodiment of the present invention.
- FIG. 7A is a conceptual diagram illustrating a change in conductivity of an optoelectronic device
- FIG. 7A is a conceptual diagram illustrating a change in conductivity of an organic thin film in response to light irradiation
- FIG. 8 is a conceptual cross-sectional view of a substrate on which a monomolecular film is formed, which is enlarged to a molecular level, for explaining a film forming process in Example 1 of the present invention.
- FIG. 9 is a conceptual cross-sectional view in which the substrate on which an oriented monomolecular film is formed in Example 1 of the present invention is enlarged to a molecular level.
- FIG. 10 is a conceptual cross-sectional view in which a substrate on which a conductive monomolecular film having a conductive network is formed for explaining a conductive network forming step after an orientation treatment in Example 1 of the present invention is enlarged to a molecular level. is there.
- FIG. 11 is a conceptual cross-sectional view in which a substrate on which a conductive network is formed and a first electrode and a second electrode are formed for explaining a counter electrode process in Example 1 of the present invention is enlarged to a molecular level. .
- FIG. 12 is a conceptual perspective view for explaining the tilt direction of the organic molecule according to the first embodiment of the present invention.
- FIG. 13 is a conceptual sectional view of an electric cable obtained in Example 2 of the present invention.
- FIG. 14 is an explanatory diagram showing a method for evaluating the orientation of conductive molecules in Example 3 of the present invention.
- the reason why the organic thin film has conductivity is that molecules constituting an assembly group of organic molecules are conjugated and polymerized.
- the conductive network is an aggregate of organic molecules connected by conjugate bonds involved in electric conduction, and is formed of a polymer having a conjugate bond chain (conjugate system).
- the conductive network is formed in the direction between the electrodes.
- the conjugated chain polymer is not strictly connected to one direction, the polymer chains of different directions, may t the organic molecules be formed between the electrodes as a whole by having a photoresponsive functional group
- the sensitivity to light is improved, and the response speed is increased. Therefore, the conductivity of the photoresponsive conductive organic thin film can be changed at high speed. It is thought that the change in conductivity when irradiated with light occurs because the photoresponsive functional group responds to light, and the effect of the response spreads to the structure of the conductive network.
- Photoresponsiveness is a property of reversibly changing the state of a molecule by light irradiation.
- Photoresponse also includes photoisomerization, which is represented by cis-trans isomerization, in which the order (arrangement) of bonding between the atoms constituting the molecule is the same and the spatial arrangement is changed. Therefore, the change in conductivity of the organic thin film is reversible, which can be returned to a predetermined state by a combination of irradiation with light having different wavelengths.
- the dopant can be any dopant such as iodine, BF- ion, alkali metal, alkaline earth metal, and the like. It may contain a trace component contained in the solution of the above or a dopant substance due to contamination unavoidably mixed from a glass container or the like. It is preferable that the polymerized conjugated bonding group is at least one conjugated bonding group selected from polypyrrole, polychenylene, polyacetylene, polydiacetylene, and polyacene.
- the terminal bonding group is at least one bond selected from siloxane (_Sio-) and -SiN- bond.
- the terminal binding group is formed by at least one elimination reaction selected from a dealcoholation reaction and a dehydrochlorination reaction.
- the molecular film formed by this method is referred to in the art as a “chemisorption film” or “self assemble film”, but is referred to as a “chemisorption film” in the present invention.
- the method is called "chemisorption method”.
- the orientation of the molecule is selected from at least one of an orientation process by lapping, a gradient solution draining process from the reaction solution after covalently bonding the molecule to the substrate surface by a desorption reaction, and a polarized light irradiation process. It is preferably formed by one process.
- the conductive region of the organic thin film is transparent to light having a wavelength in the visible region.
- the organic molecule is preferably a compound represented by the following chemical formula A '
- A is a conjugated functional group containing at least one selected from a pyrrole group, a celenylene group, an acetylene group, and a diacetylene group, which can form a conductive network by bonding through a conjugated bond;
- I a photoresponsive functional group
- D is an octane gen atom, a dissocyanate group or an alkoxyl group having 13 carbon atoms.
- At least one reactive group is at least one group selected from hydrogen and an alkyl group having 13 to 13 carbon atoms, m and n are integers, and m + n is 2 or more and 25 or less, particularly preferably 1 An integer from 0 to 20; p is an integer; 1, 2 or 3; )
- the organic molecule is preferably a compound represented by any one of the following chemical formulas BE.
- X is hydrogen, an organic group containing an ester group or an organic group containing an unsaturated group, q is an integer of 0 to 10, and m and n are integers of 1 to 20.
- the chemical formula D is chemically bonded to the base material, and then the conductive conjugate bonding group is polymerized into the following chemical formula F.
- the chemical formula E is chemically bonded to the base material, and then, the conductive conjugate bond is formed.
- the group is polymerized, the following chemical formula G is obtained.
- the organic molecules may be formed in a monomolecular layer. Further, by repeating the single-molecule layer forming step a plurality of times, the single-molecule layers may be stacked to form a single-molecule accumulation film.
- the conductive network is formed in each monolayer of the monomolecular accumulation film in the conductive network forming step, so that the conductive network is formed. You may form an accumulation
- a conductive monomolecular cumulative film may be formed by repeatedly performing a series of steps including the monomolecular layer forming step, the tilting step, and the conductive network forming step.
- At the time of forming the conductive network by the polymerization at least one polymerization selected from catalyst polymerization, energy ray irradiation polymerization, and electrolytic oxidation polymerization is performed.
- the energy ray is preferably at least one selected from ultraviolet rays, far ultraviolet rays, X-rays and electron beams.
- the energy ray is at least one selected from polarized ultraviolet rays, polarized far ultraviolet rays, and polarized X-rays, and the tilt alignment treatment and the formation of the conductive network may be performed simultaneously.
- the conductivity of the conductive network changes when the organic thin film is irradiated with light.
- each photo-responsive functional group has its own absorption characteristics. Therefore, when light having a wavelength with an excellent absorptance is used, the conductivity can be increased efficiently and quickly. It can be changed.
- the conductivity of the conductive network contained in the conductive organic thin film changes from the initial conductivity to the first conductivity.
- the initial conductivity is the conductivity of the conductive network before light irradiation.
- the conductivity of the conductive network can be changed to an arbitrary conductivity between the initial conductivity and the first conductivity. Can be.
- the conductivity of the conductive network becomes the second conductivity from the first conductivity. To the conductivity. At this time, by adjusting the amount of the second light, the conductivity of the conductive network can be changed to an arbitrary conductivity between the first conductivity and the second conductivity.
- the conductivity of the conductive network included in the organic thin film can be switched using the first light and the second light.
- this switching operation not only switching between the stable state having the first conductivity and the stable state having the second conductivity, but also the switching between the first conductivity and the second conductivity. Switch between states with any different conductivity Is possible.
- the conjugate bond chains of the conductive network exist in a specific plane.
- the conductive network formed in the monolayer is Directly connected in the direction. It has high conductivity anisotropy due to the linearity of its conductive network.
- the linearity of the conductive network means that each conjugated bond chain (conjugated system) constituting the conductive network is arranged on the same plane in the monolayer and substantially in parallel. Therefore, the conductive monolayer has a high conductivity and a uniform conductivity.
- a monomolecular layer has a conjugated bond chain having a high degree of polymerization. According to another example, it is possible to provide a conductive monomolecular film and a conductive monomolecular cumulative film having extremely good conductivity even if the film thickness is small. Also, their conductivity changes are very fast.
- a conductive organic thin film having a desired conductivity can be provided by changing the number of stacked conductive monolayers. For example, in the case of a conductive cumulative film in which the same conductive monolayer is laminated, the conductivity of the conductive network included therein is approximately proportional.
- the tilt angle of the orientation of the organic molecule may be different for each monolayer as long as the direction of the conductive network formed in all the monolayers is the same. Also, not all monolayers need to be composed of the same organic molecule. Also, a conductive monomolecular cumulative film composed of different types of organic molecules for each conductive monolayer may be used. In addition, in the case of a conductive monomolecular accumulation film, when the conductive monomolecular layer closest to the base material is bonded to the base material by a chemical bond, durability such as peel resistance is excellent. According to another example of the method of the present invention, it is possible to manufacture a photoresponsive conductive organic thin film provided with a directional conductive network.
- the direction of the conductive network may be the same as the direction of the tilt of the organic molecules constituting the organic thin film that has undergone the tilting process.
- the tilt direction of the organic molecules may not be the same as long as a conductive network having directionality is formed.
- the inclination direction of the organic molecule in the inclination treatment step means the direction of a line segment obtained by projecting the major axis of the organic molecule onto the substrate surface. Therefore, the inclination angles with respect to the substrate need not be the same.
- an organic thin film having a monomolecular layer can be formed. Further, the group of organic molecules constituting the monolayer can be accurately tilted in a predetermined direction in the tilting step. Generally, the molecules that make up the monolayer can be oriented. Furthermore, since orientation can be accurately performed, a conductive network having directionality can be easily formed in the conductive network forming step.
- a conductive network having a high degree of polymerization and being linearly connected can be formed.
- a uniform conductive monolayer can be formed due to the linearity of the conductive network.
- the organic molecules constituting the organic thin film can be easily tilted.
- each monomolecular layer can be precisely oriented. With such a monolayer oriented with high precision, a conductive network having a conjugated system having a high degree of polymerization can be formed in the conductive network forming step.
- a polarized light having a wavelength in a visible light region is used as the polarized light. According to this example, it is possible to prevent or suppress the destruction of the organic thin film due to the peeling of the organic molecules constituting the organic thin film and the destruction of the organic molecules themselves.
- an organic thin film is formed on a rubbed substrate surface. Then, the organic molecules constituting the organic thin film are inclined in a predetermined direction. Generally, the rubbing direction in the rubbing process is the same as the tilt direction of the formed organic molecules.
- Nylon or rayon cloth can be used as the rubbing cloth used in the rubbing treatment.
- the use of a nylon or rayon rubbing cloth as described above is appropriate for the purpose of improving the alignment accuracy.
- the cleaning liquid is drained in a predetermined direction.
- the substrate may be pulled up at a predetermined angle to tilt the organic molecules constituting the organic thin film.
- the organic molecules constituting the organic thin film can be easily tilted.
- each monolayer can be oriented. In general, the direction of drainage is the same as the tilt direction of the organic molecules constituting the organic thin film.
- the predetermined angle may be perpendicular to the level of the cleaning liquid. According to the above example, the lifting mechanism is simplified, and the liquid can be easily drained in a predetermined direction.
- the conductive network forming step one or more polymerization methods are applied, and the molecules constituting the organic thin film are conjugated to each other by polymerization or by polymerization and crosslinking after the polymerization to form a conductive network. Is also good. According to this example, it is possible to form a conductive network that enables electric conduction by connecting the polymerizable groups of the organic molecule by a conjugate bond.
- the type of polymerization at least one polymerization selected from electrolytic polymerization, catalytic polymerization, and energy beam irradiation polymerization can be used.
- At least one prepolymerization selected from the group consisting of polymerization and energy ray irradiation polymerization may be performed.
- a polymer formed by polymerization of one polymerizable group further undergoes a cross-linking reaction to perform the other polymerizable group.
- the other polymerizable group on the side chain of the polymer formed by polymerization is bridged.
- a conductive network including a polyacene-type concomitant system can be formed.
- a polymerization method selected from the group consisting of a catalyst polymerization method, an electrolytic polymerization method, and an energy beam polymerization method may be applied.
- a catalyst polymerization method is applied to an organic thin film composed of an organic molecule having a polymerizable group having catalytic polymerizability (hereinafter, also referred to as “catalyst polymerizable group”).
- An organic thin film composed of organic molecules having a polymerizable group (hereinafter also referred to as an electric field polymerizable group) is applied with an electric field polymerization method, and a polymerizable group (hereinafter referred to as an energy beam) polymerized by irradiation with an energy beam.
- a conductive network can be formed by applying an energy beam polymerization method to an organic thin film including an organic molecule having a polymerizable group.
- the step of performing crosslinking is at least one crosslinking step selected from the group consisting of a crosslinking step by catalytic polymerization, a crosslinking step by electrolytic polymerization, and a crosslinking step by energy beam polymerization.
- the multiple cross-linking steps include not only combinations of cross-linking steps with different actions but also combinations of steps having the same action but different reaction conditions.
- a conductive network is formed by performing a cross-linking step by irradiation with a first type of energy beam after a cross-linking step by catalytic action, and further performing a cross-linking step by irradiation with a second type of energy beam. Is also good.
- an organic molecule having a pyrrole group, a celenylene group, an acetylene group or a diacetylene group is used as an organic molecule constituting the organic thin film, and a polypyrrole conjugated system, a polychenylene conjugated system, A conductive network including a polyacetylene-type conjugated system, a polydiacetylene-type conjugated system, or a polyacetylene-type conjugated system can be formed.
- a conductive network can be formed on an organic thin film composed of a group of organic molecules having a pyrrole group or a celenylene group as the polymerizable group. .
- a conductive network including a polypyrrole-type conjugated system or a poly-Chenylene-type conjugated system can be formed by using an organic molecule having a pyrrole group or a celenylene group as the organic molecule constituting the organic thin film.
- a conductive network may be formed in the organic thin film composed of a group of molecules.
- a conductive network including a polyacetylene-type conjugated system can be formed by using an organic molecule having an acetylene group as an organic molecule constituting an organic thin film, and a polydiene can be formed by using an organic molecule having a diacetylene group.
- a conductive network including an acetylene-type conjugate system or a polyacene-type conjugate system can be formed.
- Ultraviolet rays, far ultraviolet rays, X-rays or electron beams may be used as the energy beam. According to this example, a conductive network can be efficiently formed.
- the reaction efficiency can be improved by selecting the type and energy of the energy beam having good absorption efficiency.
- many beam-irradiated polymerizable groups have absorbency to these energy beams, they can be applied to organic thin films composed of organic molecules having various types of beam-irradiated polymerizable groups.
- the tilting step and the conductive network forming step can be performed simultaneously by using polarized ultraviolet light, polarized far ultraviolet light or polarized X-ray as the energy beam.
- the organic molecules constituting the organic thin film can be inclined (orientated) in a predetermined direction, and the organic molecules can be conjugated to each other. Therefore, the process can be simplified.
- the channel portion for electrically connecting the first electrode and the second electrode is formed of a conductive organic thin film, and when the conductive organic thin film is irradiated with light, the first portion is formed.
- the conductivity between the counter electrodes is maximized, and when the first electrode and the second electrode are The rate is the smallest. If the first electrode and the second electrode are formed in a state having the maximum conductivity, a two-terminal organic optoelectronic device having a large range of change in conductivity can be provided.
- the conductivity between the electrodes can be adjusted.
- the size of the electrodes and the distance between the counter electrodes the range of change in conductivity can be adjusted.
- the conductivity of the conductive network may change according to the amount of light applied to the conductive organic thin film.
- the electric conductivity between the counter electrodes can be changed by adjusting the energy of the light absorbed by the organic thin film according to the irradiation intensity and irradiation time of the light.
- an organic optoelectronic device such as a variable resistor can be provided by the property of changing the conductivity.
- each photoresponsive functional group has its own specific absorption characteristics, so that the use of light with a wavelength with an excellent absorptance makes it possible to change the conductivity efficiently and quickly.
- the conductivity of the conductive network is changed to the first conductivity or the second conductivity, respectively, by the first light or the second light having different wavelengths applied to the conductive organic thin film, and even after quenching.
- Each of the first conductivity and the second conductivity may be maintained.
- by irradiating the first light or the second light in a state where a voltage is applied between the counter electrodes a transition is made between the stable states having the first conductivity or the second conductivity.
- the conductivity of the conductive network can be switched.
- organic optoelectronic devices such as optical variable resistors, optical switch elements, optical memory elements, and optical sensors can be used. Can be provided.
- the first conductivity or the second conductivity depends on the state before light irradiation and the amount of the first light or the second light to be irradiated. By adjusting, the conductivity of each stable state can be variably controlled.
- the photoresponsive functional group may be a photoisomerizable functional group.
- the stable state may be any state as long as the conductive network has a stable and predetermined conductivity.
- the conductivity of the conductive network is defined as the first conductivity, and the state is a stable state having the first conductivity. It is.
- the photoisomerizable functional group may be an azo group.
- the first isomer of trans-irradiation of the visible light also be isomerized into the second isomer of cis-irradiation with ultraviolet rays, the conductivity of the conductive network is changed to c the substrate
- the substrate may be an electrically insulating substrate such as glass or a resin film, or a substrate with an insulating film in which an insulating film is formed on an arbitrary substrate surface.
- the substrate can be used as it is if it is made of glass or polyimide resin because it has active hydrogen on the surface.
- Active hydrogen can be supplied by treating the substrate surface by forming a silica film, activating the substrate surface by corona discharge, plasma irradiation, or the like.
- the substrate is an electrically insulating material, it is possible to provide an organic optoelectronic device having low leakage current and excellent operation stability.
- the organic conductive film of the present invention has high conductivity and high transparency. Applications that make use of this property include electric wires, motors, generators, capacitors (capacitors), transparent electrodes (instead of ITO), semiconductor device wiring, CPU wiring (no heat generation due to electrical resistance), electromagnetic wave shielding Various applications are conceivable, such as CRT glass surface filling and Yuichi (prevention of static electricity generation).
- FIG. 12 is a conceptual diagram for explaining the tilt direction of the organic molecule.
- FIGS. 1A and 1B are conceptual diagrams in which a conductive monolayer formed on a substrate is enlarged to a molecular level.
- FIG. 1A is a cross-sectional view
- FIG. 1B is a plan view. is there.
- the terminal of the molecule is an organic molecule having a functional group capable of chemisorbing to the substrate such as a silane-based surfactant having a chlorosilyl group or an alkoxysilyl group at the terminal, the molecule is fixed to the substrate by a desorption reaction, A monomolecular film with excellent peel resistance and durability can be formed.
- a step of immersing in an organic solvent to wash and remove unadsorbed organic molecules hereinafter, also referred to as “washing step”
- a monomolecular film having no stain on the surface can be obtained. Is formed You.
- the organic molecules constituting the monomolecular film are inclined in a predetermined direction (inclination processing step).
- the organic molecules constituting the monomolecular film are oriented by tilting in a predetermined direction (hereinafter, referred to as “orientation” for the monomolecular film and the monomolecular layer).
- the rubbing treatment is performed on the surface of the monomolecular film using a rubbing device, and the organic molecules constituting the monomolecular film can be oriented in the rubbing direction.
- 41 indicates a rubbing cloth
- 42 indicates a rubbing roll.
- the organic molecules constituting the monomolecular film 4 can be oriented in the polarization direction.
- the polarized light linearly polarized light is preferable. If these orientation methods are applied, orientation can be performed with high accuracy.
- the rubbing treatment is performed on the substrate surface using a rubbing device before the monomolecular layer forming step (pretreatment step)
- the monolayer oriented to the rubbed substrate in the monomolecular film forming step can be obtained.
- a molecular film can be formed.
- the orientation direction at this time is the same as the rubbing direction.
- the substrate is pulled up while maintaining a predetermined inclination angle with respect to the liquid surface of the organic solvent 44, whereby the monomolecular film is formed.
- the constituent organic molecules can be oriented in the liquid drain direction (hereinafter, referred to as “liquid drain alignment”).
- the above three orientation methods may be applied alone, or multiple orientation methods may be used. May be applied.
- the molecules constituting the monomolecular film are conjugated to each other to form a conductive network.
- a conjugated system can be formed by polymerizing or cross-linking the molecules constituting the monomolecular film.
- a catalyst polymerization method an electrolytic polymerization method, an energy beam irradiation polymerization method, or the like can be used, and polymerization or cross-linking can be performed by applying the polymerization method.
- the catalyst polymerization method and the energy beam irradiation polymerization method can form a network efficiently because the polymerization rate is high when they are used to form a preliminary network.
- the conjugate-bondable group is an ethynyl group (including an acetylene group)
- it can be polymerized into polyacetylene by employing catalytic polymerization and / or electron beam polymerization.
- the conjugate-bondable group is a ethynyl group (including a diacetylene group)
- it can be polymerized into polydiacetylene or polyacene by employing catalytic polymerization and Z or photopolymerization.
- the group capable of conjugate bonding is a pyrrole group or a thiophene group
- it can be polymerized to polypyrrole or polythiophene by employing catalytic polymerization and / or electrolytic oxidation polymerization.
- the final step is preferably performed by an electrolytic oxidation polymerization method to form a conductive network.
- the reaction temperature may be about room temperature (25 ° C), and the reaction is performed by applying an electric field in a pure aqueous solution without using a catalyst.
- the conductive network may be formed by performing the step of polymerizing or crosslinking a plurality of times. For example, when an organic molecule having a plurality of polymerizable groups bonded by a conjugate bond is used as a film material molecule, a conductive network can be formed on a plurality of planes included in a monolayer composed of the organic molecule. Wear. Furthermore, when performing polymerization or cross-linking a plurality of times, the polymerization method may be different for each time.
- the organic molecule constituting the monomolecular film has a polymerizable group irradiated with an energy beam, it is possible to align the monomolecular film and to form a conductive network by irradiating polarized light.
- a monomolecular film composed of a group of organic molecules having a photoresponsive functional group 7 is formed, and the molecules constituting the group of organic molecules are conjugated to each other on the monomolecular film.
- a photoresponsive conductive monomolecular film 4 having a conductive network 5 connected in a predetermined direction can be manufactured.
- the first manufacturing method after the steps of forming a monolayer are repeated and the monolayers are laminated, the respective monolayers are collectively oriented in a predetermined direction, and then the monolayers are formed in each monolayer.
- the second manufacturing method comprises a step of forming a monomolecular layer, and then successively orienting the monomolecular layer to form an oriented monomolecular cumulative layer, and then forming the monomolecular cumulative film.
- a conductive network is collectively formed on each monolayer.
- the third manufacturing method is a method of repeatedly forming a monolayer, subsequently orienting the monolayer, and subsequently forming a conductive network on the monolayer. .
- the method of the first embodiment can be similarly used.
- the alignment method is an effective alignment method only before polymerization.
- the above three kinds of production methods are optimized by a method of aligning the monomolecular layer, a method of forming the conductive network, and the like. Further, it is preferable to select which manufacturing method is to be applied, depending on the number of conductive monomolecular layers in which the conductive monomolecular accumulated film is formed.
- a conductive monomolecular cumulative film having a large number of stacked layers is to be formed, it is preferable to apply the second manufacturing method or the third manufacturing method.
- a photo-alignment method or a rubbing alignment method is applied as an alignment method, and an energy beam irradiation polymerization method or an electric field polymerization method is preferable as a polymerization method. Further, as the number of layers increases, it is effective to apply a photo-alignment method as an alignment method. When the catalytic polymerization method is applied, it is difficult to form a conductive network in the lower monolayer on the substrate side.
- the second manufacturing method When the second manufacturing method is applied, it is the same as the first manufacturing method. However, since the number of alignment steps increases, it is easy to apply the photo-alignment method in the alignment processing step (tilting processing step). preferable.
- a monomolecular cumulative film composed of a group of organic molecules having a photoresponsive functional group is formed, and the monomolecular cumulative film is conjugated with the molecules constituting the group of organic molecules.
- a photoresponsive conductive monomolecular cumulative film characterized by having a conductive network connected in a predetermined direction by bonding can be manufactured.
- Figures 5A to 5D are conceptual diagrams of an example of the structure of a single-molecule cumulative film, expanded to the molecular level.
- Figure 5A shows the cumulative film using the chemisorption method, and is a cross-sectional view of the X-type conductive monomolecular cumulative film in which the orientation direction of each monolayer is the same.
- Fig. 5B the first layer is a chemisorption film, the second and subsequent layers are cumulative films formed by Langmuir-Blodgett method, and the orientation direction of each monolayer is the same direction.
- FIG. 3 is a cross-sectional view of a monomolecular accumulation film.
- FIG. 5C is a cross-sectional view of an X-type conductive monomolecular cumulative film in which the orientation direction differs for each monolayer, all of which are cumulative films formed by a chemisorption method.
- FIG. 5D is a cross-sectional view of the X-type conductive monomolecular cumulative film oriented in one of two orientation directions for each monolayer, all of which are the cumulative films formed by the chemisorption method.
- 5A to 5D 1 is a substrate, 4 is a monolayer, 5 is a conductive group formed by a conjugate bond, and 7 is a photoresponsive functional group.
- the plan view of each monolayer 4 of the various conductive monomolecular accumulation films of FIGS. 5A to D is the same as that of FIG. 1B.
- FIGS. 6A and 6B are explanatory diagrams schematically illustrating an example of the structure of a two-terminal organic optoelectronic device.
- a monolayer composed of groups is formed, the monolayer is oriented, molecules constituting the monolayer are conjugated to each other to form a conductive network 5, and are separated from each other so as to contact the conductive network 5. If the first electrode 2 and the second electrode 3 are formed, a two-terminal organic optoelectronic device can be manufactured.
- a two-terminal organic photoelectron device comprising a conductive monomolecular film 4, wherein the conductive monomolecular film 4 is composed of a group of organic molecules having a photoresponsive functional group.
- a two-terminal organic optoelectronic device having a conductive network 5 in which the constituent molecules are conjugated to each other can be provided.
- FIG. 6A shows a two-terminal organic optoelectronic device having a structure in which the first electrode 2 and the second electrode 3 are in contact with the surface of the substrate 1 and the side surface of the conductive monolayer 4, and FIG. 6B shows the first electrode.
- This is a two-terminal organic optoelectronic device having a structure in which the second electrode 2 and the second electrode 3 are formed on the surface of the conductive monomolecular film 4.
- a mask pattern is formed by photoresist, and a predetermined first electrode 2 and second electrode 2 are formed by etching.
- a two-terminal organic optoelectronic device having the structure shown in FIG. 6A or 6B can be manufactured by using different mask patterns.
- an organic molecule containing a polymerizable group can be used at an arbitrary position in the molecule.
- a plurality of conductive networks that electrically connect the second electrode 3 can be formed.
- the organic thin film is a monomolecular accumulation film, A conductive network can be formed in the child layer.
- the counter electrode step may be performed before the film forming step.
- a film having a conductive network between the electrodes of the first electrode 2 and the second electrode 3 can be formed.
- the electrode is immersed in an organic solvent in which a substance containing an electropolymerizable functional group is dissolved, and a first voltage is applied between the first electrode 2 and the second electrode 3. And applying a second voltage between the first electrode 2 or the second electrode 3 and an external electrode disposed in contact with the organic solvent and disposed above the organic thin film, the first structure is obtained.
- a film is further formed on the surface of the monomolecular film having the conductive network, and the molecules constituting the film are electrolytically polymerized to form a conductive network of the second structure.
- a substance containing an electropolymerizable functional group is applied, and a voltage is applied between the first electrode 2 and the second electrode 3.
- a polymer film having a conductive network is formed. Can be formed.
- the organic thin film does not include a monomolecular film in which the organic molecules constituting the organic thin film are arranged in a monomolecular layer, there is no difference as described above regardless of the structure of FIG. 6A or FIG. 6B.
- FIG. 7A is a schematic diagram qualitatively showing a change in conductivity with irradiation time when an organic thin film is irradiated with light of a constant intensity.
- the amount of irradiated light is proportional to the product of irradiation light intensity and irradiation time
- the change in conductivity is described as a change in current when a constant voltage is applied between the first electrode 2 and the second electrode 3.
- Conductivity of the conductive network is different from the case of c Figure 7 A as a certain value changes with irradiation, for a time sufficient to change, when exposed to light, the current value is OA (zero ampere) It may be anything. Further, FIG. 7A shows a case where the current value is decreased by light irradiation, but may be increased. These depend on the constituent materials and structure of the organic thin film or the structure of the conductive network.
- FIG. 7B shows the photofunctionalized functional groups that undergo photoisomerization, and the first and second electric conductivities associated with the isomerization by irradiation with the first light or the second light, respectively.
- FIG. 7 is a conceptual diagram showing a switching operation by a transition between stable states having the following.
- Line L 1 and line L 2 in FIG. 7B are irradiated with the first light and the second light, respectively (P 1 () N , P 20N ) or light-shielded (P 1 () FF , P 20FF ).
- 7 line L 3 of the B representing the state represents the response current value when the current value when the first light is irradiated is irradiated I physician second light is I 2.
- the figure shows the switching of the current flowing between the first electrode 2 and the second electrode 3. From line L3 in Fig. 7B, current switching is triggered by the first light and the second light, and is a reset-set type (R-S type). It can be seen that the operation is the same as that of the lip flip.
- R-S type reset-set type
- the case where only one of the different isomers was included was regarded as a stable state having the first conductivity
- the case where only the other isomer was included was regarded as the stable state having the second electric conductivity. That is, two completely isomerized states are stable states having the first conductivity or the second conductivity. In this case, the conductivity does not change even if the first stable state is further irradiated with the first light. The same applies to the case where the second stable state is irradiated with the second light.
- the operation of the switch element for the current flowing between the first electrode and the second electrode has been exemplified.However, since the conductivity of the organic thin film changes due to light irradiation, light control is performed. It can be used as a variable resistor. In the case of an organic thin film composed of a molecule group having a photoisomerizable functional group as a photoresponsive functional group, a first current is applied between the first and second electrodes or a first voltage is applied thereto. Alternatively, by irradiating the second light and reading out a voltage change or a current change between the electrodes of the first electrode 2 and the second electrode 3, the voltage change or the current change can be respectively performed as an optical sensor or with the irradiation time.
- a two-terminal organic optoelectronic device including a photoresponsive conductive monomolecular film will be described with reference to FIGS.
- an ethynyl group (—C ⁇ C-1), which forms a conductive network by conjugated bonding through polymerization
- active hydrogen for example, a hydroxyl group (- OH)
- react trickle Roroshiriru groups - S i C 1 3
- diluted to 1% in the dehydrated dimethylsilicone solvent prepare a chemical adsorption solution containing Did ⁇
- rubbing treatment was performed in parallel with the direction from the first electrode 22 to the second electrode 23 using a rubbing device used for producing a liquid crystal alignment film.
- a rubbing roll 42 of 7 cm in diameter wrapped with a rubbing cloth 41 made of rayon (YA-200-R manufactured by Yoshikawa Kako Co., Ltd.) was used, the Ep width was 11.7 mm, and the rotation speed of the roll was used.
- the rubbing treatment was performed on the monomolecular film 24a, but before the monomolecular layer forming step, the rubbing treatment was performed on the glass substrate 21 under the same conditions, and the rubbing treatment was performed.
- a nickel thin film is vapor-deposited on the entire surface, and the first electrode 22 and the second electrode 23 having a length of 30 m and a length of 30 m are etched using photolithography to etch the first electrode 22 and the second electrode 23. Formed.
- a two-terminal organic optoelectronic device comprising a conductive monomolecular film 24 c, wherein the conductive monomolecular film 24 c is composed of a group of organic molecules having an azo group, and forms a conductive monomolecular film.
- a two-terminal organic optoelectronic device having a conductive network 25 in which the constituent molecules are connected in a predetermined direction by polyacetylene-type conjugate bonds was manufactured (Fig. 11).
- the electrodes of the first electrode 22 and the second electrode 23 are connected by a polyacetylene-type conductive network 25. Then, when a voltage of several volts was applied between the first electrode 22 and the second electrode 23, a current of several hundred nanoamperes (approximately 1018 for 1 ⁇ ) flowed. However, the conductive monomolecular film 24c was irradiated with visible light before the measurement. Next, when the conductive monomolecular film 24c was subsequently irradiated with ultraviolet rays, the azo group was transferred from the trans-form to the cis-form, and the current value became almost OA. Then, upon irradiation with visible light, the azo group was transferred from the cis-form to the trans-form, and the original conductivity was reproduced. Reference numeral 6 denotes the collected irradiation light.
- the decrease in conductivity due to the irradiation of ultraviolet light is caused by polyacetylene-type conjugate bond in the conductive monomolecular film 24c due to photo-catalyst of azo group (transition from trans type to cis type). This is considered to be caused by a decrease in the conductivity of the conductive network 25.
- the electric current flowing between the first electrode 22 and the second electrode 23 could be switched by controlling the conductivity of the conductive network 25.
- the resistance increases when the degree of polymerization is low. That is, the on-current is reduced.
- a dopant substance having a charge-transferring functional group for example, an aluminum metal or an ammonium salt
- the ON current could be increased.
- iodine is doped into the conductive monomolecular film 24c, when a voltage of 1 V is applied between the first electrode 22 and the second electrode 23, 0.2 m is applied. A current flowed.
- a conductive substrate such as a metal
- a monomolecular film may be formed on the surface of the conductive substrate via an insulating thin film.
- the substrate itself since the substrate itself is not charged, the organic light The operational stability of electronic devices has been improved.
- the distance between the first electrode 22 and the second electrode 23 may be reduced or the electrode width may be increased. If a larger on-current is required, a monomolecular film may be accumulated or a film having a conductive network may be formed between the first electrode 22 and the second electrode 23. .
- the conductive network could be similarly formed using the electrolytic polymerization method or the energy beam irradiation polymerization method such as light, electron beam, or X-ray.
- a conjugated system such as a polydiacetylene-type, polyacene-type, polypyrrole-type, and polychenylene-type can be used as the conductive network.
- a pyrrole group, a celenylene group, a diacetylene group, or the like is suitable as the polymerizable group in addition to the acetylene group.
- the Langmuir-Projet method can be applied to the production of a monomolecular film or a monomolecular accumulation film.
- the first and second electrodes can be used for electrolytic polymerization. That is, by applying a voltage between the first and second electrodes of the organic thin film composed of a group of organic molecules having a pyrrole group or a celenylene group as an electropolymerizable functional group, The organic thin film between the second electrodes can be selectively electropolymerized.
- a substance containing a pyrrole group or a chenylene group is formed. Dipped in dissolved organic solvent and before A first voltage is applied between the first electrode and the second electrode, and an external device is disposed in contact with the first or second electrode and the organic solvent and disposed above the monomolecular film.
- a second voltage between the electrodes a film can be further formed on the surface of the monomolecular film, and at the same time, a conductive network can be formed on the monomolecular film and the film.
- the organic optoelectronic device has a channel portion composed of a monomolecular layer having a conductive network and a polymer film-like coating layer.
- a monomolecular film composed of a group of organic molecules having a pyrrole group or a celenylene group, a first electrode, and a second electrode are formed on a substrate, and the conductive film having the first structure is formed on the monomolecular film.
- the organic optoelectronic device has a channel portion composed of a monolayer having a conductive network and a coating layer in the form of a polymer film.
- a monomolecular film or a monomolecular accumulation film composed of a group of organic molecules having an acetylene group, a diacetylene group, or the like, which is a functional group polymerized by an energy beam as a polymerizable group, may have an ultraviolet ray, a far ultraviolet ray, an electron beam,
- a conductive network can be formed by irradiating an energy beam such as a line and polymerizing the molecules constituting the monomolecular film or the monomolecular cumulative film.
- a compound represented by the following chemical formula (3) was used.
- the compound of the formula (3) was diluted to 1 wt% with a dehydrated dimethyl silicone solvent to prepare a chemisorption solution.
- a glass fiber having a diameter of 1 mm was immersed in this chemisorption solution at room temperature (25 ° C) for 1 hour, and a dechlorination reaction was performed on the surface of the glass fiber to form a thin film.
- the unreacted compound was washed away with a non-aqueous solution of chloroform.
- the glass fiber on which the monomolecular film was formed was immersed in a chloroform solution to be washed, and when the glass fiber was pulled out of the chloroform solution, the monofilament was oriented by draining in the length direction.
- a nickel thin film was formed by vapor deposition on a part of the end of the glass fiber.
- electrolysis of 5 VZ cm was applied between the electrodes to perform electrolytic oxidation polymerization.
- the conditions of the electrolytic oxidation polymerization were a reaction temperature of 25 ° C. and a reaction time of 8 hours.
- a conductive network was formed by electrolytic polymerization, and the two electrodes were electrically connected.
- a conjugate bond is formed in a self-organizing manner along the direction of the electric field, so that when the polymerization is completely completed, both electrodes are electrically connected by a conductive network.
- the chemical formula of the obtained organic conductive film is shown in the following (5).
- the thickness of the obtained organic conductive film was about 2. 0 nm, polypyrrole thickness of Ichiru part about 0. 2 nm, the length of the organic conductive film was 1 Omm, width 1 0 0 m t The obtained organic conductive film was transparent under visible light.
- the obtained organic conductive film was subjected to AFM-CITS mode using a commercially available atomic force microscope (AFM) (manufactured by Seiko Instruments Inc., SAP 380 ON) at a voltage of lmV and a current of 160 nA.
- AFM atomic force microscope
- the conductivity p under the conditions is as follows: ⁇ ): 1 X 10 3 S / cm at room temperature (25 ° C) without doping.
- FIG. 13 shows a cross-sectional view of the obtained electric wire.
- 50 is an electric cable
- 51 is a glass core wire
- 52 is a polypyrrole electrolytic oxidation-polymerized film
- 53 is a coating insulating film made of room-temperature-curable silicone rubber.
- the electric cable may form a collective electric wire including a plurality of core wires electrically insulated from each other.
- metal can be used in addition to glass for the core wire when making electric wires.
- metal when an oxide is formed on the surface, a monomolecular film is easily formed. (Example 3)
- Example 1 whether or not the conductive molecules are oriented is determined by forming a liquid crystal cell 60 as shown in FIG. 15 and sandwiching the liquid crystal cell between polarizing plates 67 and 68 and irradiating light from the back surface. Can be confirmed by observing from the 70 position.
- the liquid crystal cell 60 is formed by holding the glass plates 61 and 63, on which the conductive molecular films 62 and 64 are respectively formed, with the conductive molecular film on the inner side and maintaining a gap distance of 5 to 6 / zm. sealing the periphery with adhesive 6 5, the liquid crystal composition 6 6 (a nematic liquid crystal, for example, made by Chisso Corporation "LC, MT - 5 0 8 7 LA") inside c to create by injecting
- the back substrate is not transparent, use only one polarizing plate on the upper side, irradiate light from the surface, and observe with reflected light.
- Example 2 Since the method of preparing the conductive molecular film of Example 2 is the same as that of Example 1, it can be inferred that the film is oriented.
- the density of the device has been increased and the device density has been improved.
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Description
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US10/451,166 US7078103B2 (en) | 2000-12-26 | 2001-12-25 | Conductive organic thin film, process for producing the same, and organic photoelectronic device, electric wire, and electrode each employing the same |
AT01272304T ATE491231T1 (de) | 2000-12-26 | 2001-12-25 | Leitfähiger organischer dünnfilm, prozess zu seiner herstellung und dessen verwendung in einem organischen photolektronischen bauelement, und einer elektrode |
EP01272304A EP1355323B1 (en) | 2000-12-26 | 2001-12-25 | Conductive organic thin film, process for producing the same, and organic photoelectronic device, and electrode employing the same |
DE60143625T DE60143625D1 (de) | 2000-12-26 | 2001-12-25 | Leitfähiger organischer dünnfilm, prozess zu seiner herstellung und dessen verwendung in einem organischen photolektronischen bauelement, und einer elektrode |
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PCT/JP2001/011325 WO2002052659A1 (fr) | 2000-12-26 | 2001-12-25 | Couche mince organique conductrice, son procede de fabrication, composant electronique mettant cette couche mince en application, cable electrique, electrode, compose de pyrrolyle et compose de thienyle |
PCT/JP2001/011324 WO2002052581A1 (fr) | 2000-12-26 | 2001-12-25 | Film fin organique conducteur et son procede de fabrication, dispositif photoelectrique organique, fil electrique et electrode mettant en oeuvre ledit film |
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TW555790B (en) | 2000-12-26 | 2003-10-01 | Matsushita Electric Ind Co Ltd | Conductive organic thin film, process for producing the same, and organic photoelectronic device, electric wire, and electrode aech employing the same |
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Also Published As
Publication number | Publication date |
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TW555790B (en) | 2003-10-01 |
US20040056237A1 (en) | 2004-03-25 |
CN1483205A (zh) | 2004-03-17 |
EP1355323A4 (en) | 2006-11-22 |
US20040109954A1 (en) | 2004-06-10 |
US20060257588A1 (en) | 2006-11-16 |
EP1355323B1 (en) | 2010-12-08 |
US7220468B2 (en) | 2007-05-22 |
US7198829B2 (en) | 2007-04-03 |
EP1357612A4 (en) | 2007-01-03 |
ATE491231T1 (de) | 2010-12-15 |
EP1355323A1 (en) | 2003-10-22 |
WO2002052659A1 (fr) | 2002-07-04 |
EP1357612A1 (en) | 2003-10-29 |
DE60143625D1 (de) | 2011-01-20 |
US7078103B2 (en) | 2006-07-18 |
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