Conductive organic thin film, process for producing the same, electronic device employing the same, electrical cable, electrode, pyrrolyl compound, and theienyl compound

1. A conductive organic thin film of oriented organic molecules, comprising: at one end of the oriented organic molecules, a terminal bonding group that is covalently bonded to a substrate surface, wherein the terminal bonding group is at least one selected from a siloxane (—SiO—)-containing bonding group and a silicon nitride (—SiN—)-containing bonding group, wherein the Si atomic nucleus and the N atomic nucleus can be additionally furnished with other bonded groups with corresponding valence; a conjugate bonding group that is located at any portion of the oriented organic molecules, away from the terminal bonding group covalently bonded to the substrate surface, wherein the conjugate bonding group is polymerized with the conjugate bonding groups of the other oriented organic molecules; a polar functional group that does not include active hydrogen and that is located between the terminal bonding group and the conjugate bonding group on the oriented organic molecules, wherein the polar functional group that does not include active hydrogen is at least one group selected from an ester group (—COO—), an oxycarbonyl group (—COO—), a carbonyl group (—CO—), and a carbonate group (—OCOO—), and bonded to both sides of the polar functional group are alkylene groups which are —(CH2)m- and —(CH2)n-, where m and n are integers; wherein the oriented organic molecules with their conjugate bonding group polymerized with the conjugate bonding groups of the other oriented organic molecules, form a conduction network, and wherein the organic molecules are oriented by at least one orientation method selected from orientation by letting the reaction solution run off a tilted surface after covalently bonding the organic molecules to the substrate surface in an elimination reaction, orientation by a process of irradiating the organic molecules with polarized light, and orientation by rocking the organic molecules during the polymerization step.

2. The conductive organic thin film according to claim 1 ,

wherein the polymerization is at least one selected from polymerization through electrolytic oxidation, catalytic polymerization, and polymerization through energy beam irradiation.

3. The conductive organic thin film according to claim 2 ,

wherein polymerization through electrolytic oxidation is the final polymerization that is performed.

4. The conductive organic thin film according to claim 1 ,

wherein a conductivity (ρ) of the conductive organic thin film without dopants is at least 1 S/cm at room temperature (25° C.).

5. The conductivc organic thin film according to claim 4 ,

wherein the conductivity (ρ) of the conductive organic thin film without dopants is at least 1×10 3 S/cm at room temperature (25° C.).

6. The conductive organic thin film according to claim 5 ,

wherein the conductivity (ρ) of the conductive organic thin film without dopants is at least 5.5×10 5 S/cm at room temperature (25° C.).

7. The conductive organic thin film according to claim 6 ,

wherein the conductivity (ρ) of the conductive organic thin film without dopants is at least 1×10 7 S/cm at room temperature (25° C.).

8. The conductive organic thin film according to claim 1 ,

wherein the conjugate bonding group that is polymerized is at least one conjugate bonding group selected from polypyrrole, polythienylene, polyacetylene, polydiacetylene, and polyacene.

9. The conductive organic thin film according to claim 1 ,

wherein the conduction region of the organic thin film is transparent with respect to light of wavelengths in the visible region.

10. The conductive organic thin film according to claim 1 ,

wherein a molecular unit forming the conduction network is expressed by a chemical formula (A) or (B) shown below:

wherein in chemical formulae (A) and (B), X is hydrogen or an organic group including an unsaturated group, q is an integer of 0 to 10, Z is an ester group (—COO—), an oxycarbonyl group (—OCO—), a carbonyl group (—CO—), or a carbonate group (—OCOO—), E is hydrogen or an alkyl group with a carbon number of 1 to 3, m and n are integers with m+n being at least 2 and not more than 25 and preferably at least 10 and not more than 20, and p is an integer of 1, 2, or 3.

11. A conductive organic thin film, comprising oriented organic molecules, comprising: at one end of the oriented organic molecules, a terminal bonding group that is covalently bonded to a substrate surface, wherein the terminal bonding group is at least one selected from a siloxane (—SiO—)-containing bonding group and a silicon nitride (—SiN—)-containing bonding group, wherein the Si atomic nucleus and the N atomic nucleus can be additionally furnished with other bonded groups with corresponding valence; a conjugate bonding group that is located at any portion of the oriented organic molecules, away from the terminal bonding group covalently bonded to the substrate surface, wherein the conjugate bonding group is polymerized with the conjugate bonding groups of the other oriented organic molecules; a polar functional group that does not include active hydrogen and that is located between the terminal bonding group and the conjugate bonding group on the oriented organic molecules, wherein the polar functional group that does not include active hydrogen is at least one group selected from an ester group (—COO—), an oxycarbonyl group (—OCO—), a carbonyl group (—CO—), and a carbonate group (—OCOO—), and bonded to both sides of the polar functional group are alkylene groups which are —(CH2)m- and —(CH2)n-, where m and n are integers; wherein the oriented organic molecules with their conjugate bonding group polymerized with the conjugate bonding groups of the other oriented organic molecules, form a conductive network, wherein the conductive network is at least one type of polymer selected from polypyrrole and polythienylene, and wherein a conductivity (p) of the conductive organic thin film without dopants is at least 1×10 7 S/cm at room temperature (25° C.).

12. A method for manufacturing a conductive organic thin film, comprising: forming an organic thin film, by bringing a compound into contact with a substrate whose surface has active hydrogen or to which active hydrogen has been added, and covalently bonding the two through an elimination reaction, wherein the compound is made of organic molecules including, at one end, a terminal bonding group that can be covalently bonded to a substrate surface, wherein the terminal bonding group is at least one selected from a siloxane (—SiO—)-containing bonding group and a silicon nitride (—SiN—)-containing bonding group, and wherein the Si atomic nucleus and the N atomic nucleus can be additionally furnished with other bonded groups with corresponding valence; a conjugated bondable group that is located at any portion of the organic molecules, away from the terminal group, and that can be polymerized with other organic molecules; and a polar functional group that does not include active hydrogen and that is located at any portion between the terminal bonding group and the conjugated bondable group, wherein the polar functional group that does not include active hydrogen is at least one group selected from an ester group (—COO—), an oxycarbonyl group (—COO—), a carbonyl group (—CO—), and a carbonate group (—OCOO—), and bonded to both sides of the polar functional group are alkylene groups which are —(CH2)m- and —(CH2)n-, where m and n are integers; orienting the organic molecules making up the organic thin film either by tilting them in a predetermined direction or by giving them orientation while polymerizing them in a subsequent polymerization step; and in a polymerization step, conjugatively bonding the conjugated bondable groups to one another by at least one polymerization method selected from polymerization through electrolytic oxidation, catalytic polymerization, and polymerization through energy beam irradiation, so as to form a conduction network.

13. The method for manufacturing a conductive organic thin film according to claim 12 ,

wherein the terminal functional group is a halogenated silyl group, an alkoxysilyl group, or an isocyanate group, and forms covalent bonds with the active hydrogen of the substrate surface by at least one elimination reaction selcered from a dehydrochlorination reaction, dealcoholization reaction, and deisocyanation reaction.

14. The method for manufacturing a conductive organic thin film according to claim 12 ,

wherein the conjugated bondable group is at least one group selected from a pyrrolyl group, a thienyl group, an ethynyl group including acetylene, and a diethynyl group including diacetylene.

15. The method for manufacturing a conductive organic thin film according to claim 12 ,

wherein in the final stage of the polymerization step, the conduction network is completed by polymerization through electrolytic oxidation.

16. The method for manufacturing a conductive organic thin film according to claim 12 ,

wherein the organic molecules are expressed by a chemical formula (C) or (D) shown below:

wherein in chemical formulae (C) and (D), X is hydrogen or an organic group including an unsaturated group, q is an integer of 0 to 10, Z is an ester group (—COO—), an oxycarbonyl group (—OCO—), a carbonyl group (—CO—), or a carbonate group (—OCOO—), E is a halogen atom, an isocyanate group, or an alkoxysilyl group with a carbon number of 1 to 3, m and n are integers with m+n being at least 2 and not more than 25 and preferably at least 10 and not more than 20, and p is an integer of 1, 2, or 3.

17. The method for manufacturing a conductive organic thin film according to claim 12 ,

wherein the organic molecules are formed in monomolecular layers.

18. The method for manufacturing a conductive organic thin film according to claim 17 ,

wherein a monomolecular stacked film is formed by layering monomolecular layers through repeating the monomolecular layer formation step a plurality of times.

19. The method for manufacturing a conductive organic thin film according to claim 18 ,

wherein a conductive monomolecular stacked film is formed by collectively forming a conduction network in each of the monomolecular layers of the monomolecular stacked film in the conduction network formation step after the monomolecular layer formation step and the tilting step have been repeatedly performed in intemation.

20. The method for manufacturing a conductive organic thin film according to claim 12 ,

wherein a conductive monomolecular stacked film is formed by repeatedly performing the monomolecular layer formation step, the tilting step, and the conduction network formation step.

21. The method for manufacturing a conductive organic thin film according to claim 12 ,

wherein the energy beam is at least one selected from ultraviolet radiation, far ultraviolet radiation, X-rays, and an electron beam.

22. The method for manufacturing a conductive organic thin film according to claim 21 ,

wherein the energy beam is at least one selected from polarized ultraviolet radiation, polarized far ultraviolet radiation, and polarized X-rays, and the tilt orientation process and formation of the conduction network process are performed at the same time.

23. The method for manuflicturing a conductive organic thin film according to claim 12 ,

wherein dopants are added during or after the conduction network is formed.

24. An electrode that is transparent with respect to light of wavelengths in the visible light region; wherein the electrode is formed by a conductive organic thin film of oriented organic molecules comprising: at one end of the oriented organic molecules, a terminal bonding group that is covalently bonded to a substrate surface, wherein the terminal bonding group is at least one selected from a siloxane (—SiO—)-containing bonding group and a silicon nitride (—SiN—)-containing bonding group, wherein the Si atomic nucleus and the N atomic nucleus can be additionally furnished with other bonded groups with corresponding valence; a conjugate bonding group that is located at any portion of the oriented organic molecules, away from the terminal bonding group covalently bonded to the substrate surface, wherein the conjugate bonding group is polymerized with the conjugate bonding groups of the other oriented organic molecules; a polar functional group that does not include active hydrogen and that is located between the terminal bonding group and the conjugate bonding group on the oriented organic molecules, wherein the polar functional group that does not include active hydrogen is at least one group selected from an ester group (—COO—), an oxycarbonyl group (—OCO—), a carbonyl group (—CO—), and a carbonate group (—OCOO—), and bonded to both sides of the polar functional group are alkylene groups which are —(—CH2)m- and —(CH2)n-, where m and n are integers; wherein the oriented organic molecules with their conjugate bonding group is polymerized with the conjugate bonding groups of the other oriented organic molecules, form a conduction network.

25. An electric cable comprising a core line, a conductive organic thin film formed in a longitudinal direction of a surface of the core line, and an insulating coating that covers the conductive organic thin film, wherein the conductive organic thin film is made of oriented organic molecules comprising: at one end of the oriented organic molecules, a terminal bonding group that is covalently bonded to a substrate surface of the core line, wherein the terminal bonding group is at least one selected from a siloxane (—SiO—)-containing bonding group and a silicon nitride (—SiN—)-containing bonding group, wherein the Si atomic nucleus and the N atomic nucleus can be additionally furnished with other bonded groups with corresponding valence; a conjugate bonding group that is located at any portion of the oriented organic molecules, away from the terminal bonding group covalently bonded to the substrate surface, wherein the conjugate bonding group is polymerized with the conjugate bonding groups of the other oriented organic molecules; a polar functional group that does not include active hydrogen and that is located between the terminal bonding group and the conjugate bonding group on the oriented organic molecules, wherein the polar functional group that does not include active hydrogen is at least one group selected from an ester group (—COO—), an oxycarbonyl group (—OCO—), a carbonyl group (—CO—), and a carbonate group (—OCOO—), and bonded to both sides of the polar functional group are alkylene groups which are —(CH2)m- and —(CH2)n-, where m and n are integers; wherein the oriented organic molecules with their conjugate bonding group polymerized with the conjugate bonding groups of the other oriented organic molecules, form a conduction network.

26. The electric cable according to claim 25 ,

wherein the electric cable forms an electric wiring assembly including a plurality of core wires that are electrically insulated from one another.

27. The electric cable according to claim 25 ,

wherein the core wire is glass or metal.

28. An electrode that is transparent with respect to light of wavelengths in the visible radiation region, wherein the electrode is a conductive organic thin film of organic molecules comprising: at one end of the organic molecules, a terminal bonding group that is covalently bonded to a substrate surface, wherein the terminal bonding group is at least one selected from a siloxane (—SiO—)-containing bonding group and a silicon nitride (—SiN—)-containing bonding group, wherein the Si atomic nucleus and the N atomic nucleus can be additionally furnished with other bonded groups with corresponding valence; a conjugate bonding group that is located at any portion of the organic molecules, away from the terminal bonding group covalently bonded to the substrate surface, wherein the conjugate bonding group is polymerized with the conjugate bonding groups of the other organic molecules; a polar functional group that does not include active hydrogen and that is located between the terminal bonding group and the conjugate bonding group on the organic molecules, wherein the polar functional group that does not include active hydrogen is at least one group selected from an ester group (—COO—), an oxycarbonyl group (—OCO—), a carbonyl group (—CO—), and a carbonate group (—OCOO—), and bonded to both sides of the polar functional group are alkylene groups which are —(CH2)m- and —(CH2)n-, where m and n are integers; wherein the organic molecules are oriented and their conjugate bonding groups are polymerized, forming a conduction network.

29. A conductive organic thin film of organic molecules which are oriented and their conjugate bonding groups are polymerized to form a conductive network, wherein the oriented organic molecules comprise a pyrrolyl compound or a thienyl compound expressed by a chemical formula (C) or (D) shown below:

wherein in the chemical formulae (C) and (D), X is hydrogen or an organic group including an unsaturated group, q is an integer of 0 to 10, Z is an ester group (—COO—), an oxycarbonyl group (—OCO—), a carbonyl group (—CO—), or a carbonate group (—OCOO—), E is a halogen atom, an isocyanate group, or an alkoxysilyl group with a carbon number of 1 to 3, m and n are integers with m+n being at least 2 and not more than 25 and preferably at least 10 and not more than 20, and p is an integer of 1, 2, or 3.