The invention relates to a self-doping type electrically conducting polymer comprising an isothianaphthene or thiophene skeleton where the polymer chains are crosslinked preferably through a sulfone bond which is imparted with water resistance and solvent resistance; a production process thereof; an
The invention relates to a self-doping type electrically conducting polymer comprising an isothianaphthene or thiophene skeleton where the polymer chains are crosslinked preferably through a sulfone bond which is imparted with water resistance and solvent resistance; a production process thereof; an electrically conducting composition film obtained by coating a composition containing the self-doping type electrically conducting polymer on a substrate and heating it; a product coated using the composition; and an electronic device containing the self-doping type electrically conducting polymer.
대표청구항▼
The invention claimed is: 1. A self-doping type electrically conducting polymer comprising crosslinked polymer chains, wherein the crosslinking is formed through a sulfone bond and the polymer contains an isothianaphthene skeleton having a sulfonic acid group. 2. The self-doping type electrically
The invention claimed is: 1. A self-doping type electrically conducting polymer comprising crosslinked polymer chains, wherein the crosslinking is formed through a sulfone bond and the polymer contains an isothianaphthene skeleton having a sulfonic acid group. 2. The self-doping type electrically conducting polymer as claimed in claim 1, wherein the sulfone bond is contained in an amount of from 1 to 90 mol % based on the repeating unit of the polymer. 3. The self-doping type electrically conducting polymer as claimed in claim 1, wherein the polymer chains are crosslinked through a bond having a binding energy from 0.5 to 2 eV lower than the binding energy of the sulfonic acid group as measured by X-ray photoelectron spectrometry. 4. The self-doping type electrically conducting polymer as claimed in claim 1, wherein the crosslinked structure through a sulfone bond is a isothianaphthene structure represented by formula (1)' wherein R1 to R3 each independently represents a hydrogen atom, a linear or branched alkyl group having from 1 to 20 carbon atoms, a linear or branched alkoxy group having from 1 to 20 carbon atoms, a linear or branched alkenyl group having from 2 to 20 carbon atoms, a linear or branched alkenyloxy group having from 2 to 20 carbon atoms, a hydroxyl group, a halogen atom, a nitro group, a cyano group, a trihalomethyl group, a phenyl group, a substituted phenyl group or a--B1--SO3-M+ group, B1 and B2 each independently represents--(CH2)p--(O)q--(CH2)r--, p and r each independently represents 0 or an integer of 1 to 3, q represents 0 or 1, X represents a polymer chain selected from the group consisting of a polypyrrole structure, a polythiophene structure, a polycarbazole structure, a polyaniline structure and an arylenevinylene structure which bonds to B2 via an aromatic ring or a heterocyclic ring contained in the polymer chain, and M+ represents a hydrogen ion, an alkali metal ion or a quaternary ammonium ion. 5. The self-doping type electrically conducting polymer as claimed in claim 1, wherein the crosslinked structure through a sulfone bond is a structure represented by formula (2): wherein R1 to R6 each independently represents a hydrogen atom, a linear or branched alkyl group having from 1 to 20 carbon atoms, a linear or branched alkoxy group having from 1 to 20 carbon atoms, a linear or branched alkenyl group having from 2 to 20 carbon atoms, a linear or branched alkenyloxy group having from 2 to 20 carbon atoms, a hydroxyl group, a halogen atom, a nitro group, a cyano group, a trihalomethyl group, a phenyl group, a substituted phenyl group or a--B1--SO3-M+ group, B1 represents--(CH2)p--(O)q--(CH2)r--, p and r each independently represents 0 or an integer of 1 to 3, q represents 0 or 1, and M+ represents a hydrogen ion, an alkali metal ion or a quaternary ammonium ion. 6. The self-doping type electrically conducting polymer as claimed in claim 5, wherein the crosslinked structure through a sulfone bond is a structure represented by formula (3) wherein B1 represents--(CH2)p--(O)q--(CH2)r--, p and r each independently represents 0 or an integer of 1 to 3, q represents 0 or 1, and M+ represents a hydrogen ion, an alkali metal ion or a quaternary ammonium ion. 7. A process for producing the self-doping type electrically conducting polymer containing a crosslinked structure through a sulfone bond represented by formula (2) described in claim 5, comprising dehydration-condensing self-doping type electrically conducting polymers having a structure represented by formula (7) wherein R1 to R3 each independently represents a hydrogen atom, a linear or branched alkyl group having from 1 to 20 carbon atoms, a linear or branched alkoxy group having from 1 to 20 carbon atoms, a linear or branched alkenyl group having from 2 to 20 carbon atoms, a linear or branched alkenyloxy group having from 2 to 20 carbon atoms, a hydroxyl group, a halogen atom, a nitro group, a cyano group, a trihalomethyl group, a phenyl group, a substituted phenyl group or a--B1--SO3-M+ group, with the proviso that at least one of R1 to R3 is a hydrogen atom, B1 represents--(CH2)p--(O)q--(CH2)r--, p and r each independently represents 0 or an integer of 1 to 3, q represents 0 or 1, and M+ represents a hydrogen ion, an alkali metal ion or a quaternary ammonium ion. 8. A process for producing the self-doping type electrically conducting polymer containing a crosslinked structure through a sulfone bond represented by formula (2) described in claim 5, comprising dehydration-condensing self-doping type electrically conducting polymers having a structure represented by formula (7) and/or formula (8): wherein R1 to R3 and R7 to R10 each independently represents a hydrogen atom, a linear or branched alkyl group having from 1 to 20 carbon atoms, a linear or branched alkoxy group having from 1 to 20 carbon atoms, a linear or branched alkenyl group having from 2 to 20 carbon atoms, a linear or branched alkenyloxy group having from 2 to 20 carbon atoms, a hydroxyl group, a halogen atom, a nitro group, a cyano group, a trihalomethyl group, a phenyl group, a substituted phenyl group or a--B1--SO3-M+ group, with the proviso that at least one of R7 to R10 is a hydrogen atom, B1 represents--(CH2)p--(O)q--(CH2)r--, p and r each independently represents 0 or an integer of 1 to 3, q represents 0 or 1, and M+ represents a hydrogen ion, an alkali metal ion or a quaternary ammonium ion. 9. A process for producing the self-doping type electrically conducting polymer containing a crosslinked structure through a sulfone bond represented by formula (3) described in claim 6, comprising dehydration-condensing self-doping type electrically conducting polymers obtained by (co)polymerizing a monomer represented by formula (9): wherein B1 represents--(CH2)p--(O)q--(CH2)r--, p and r each independently represents 0 or an integer of 1 to 3, q represents 0 or 1, and M+ represents a hydrogen ion, an alkali metal ion or a quaternary ammonium ion. 10. The process for producing a self-doping type electrically conducting polymer as claimed in claim 7, wherein the dehydration condensation reaction is performed by a heat treatment at a temperature range of 210 to 350° C. 11. A self-doping type electrically conducting polymer obtained by the production process described in claim 7. 12. An electrically conducting composition comprising the self-doping type electrically conducting polymer described in claim 1, and a solvent. 13. A method for producing an electrically conducting film, comprising coating the electrically conducting composition described in claim 12 on a substrate and heating it. 14. The method for producing an electrically conducting film as claimed in claim 13, wherein the self-doping type electrically conducting polymer having a structure represented by formula (7) and/or formula (8) is applied onto a substrate surface and then the substrate is heated at a temperature of 210 to 350° C. for 1 to 600 seconds, wherein R1 to R3 and R7 to R10 each independently represents a hydrogen atom, a linear or branched alkyl group having from 1 to 20 carbon atoms, a linear or branched alkoxy group having from 1 to 20 carbon atoms, a linear or branched alkenyl group having from 2 to 20 carbon atoms, a linear or branched alkenyloxy group having from 2 to 20 carbon atoms, a hydroxyl group, a halogen atom, a nitro group, a cyano group, a trihalomethyl group, a phenyl group, a substituted phenyl group or a--B1--SO3-M+ group, with the proviso that at least one of R7 to R10 is a hydrogen atom, B1 represents--(CH2)p--(O)q--(CH2)r--, p and r each independently represents 0 or an integer of 1 to 3, q represents 0 or 1, and M+ represents a hydrogen ion, an alkali metal ion or a quaternary ammonium ion. 15. The self-doping type electrically conducting polymer as claimed in claim 1, wherein one of the crosslinked polymer chains contains an isothianaphthene skeleton having a sulfonic acid group and another of the crosslinked polymer chains is selected from the group consisting of a polypyrrole structure, a polythiophene structure, a polycarbazole structure, a polyaniline structure and an arylenevinylene structure. 16. An electrically conducting film produced by the method described in claim 13. 17. The electrically conducting film as described in claim 16, wherein the film thickness is from 1 to 1,000 nm. 18. A coated product comprising a shaped body having coated on the surface thereof the self-doping type electrically conducting polymer described in claim 1. 19. A coated product comprising a substrate as a shaped body, wherein one surface, both surfaces or the entire surface of the substrate is coated with the self-doping type electrically conducting polymer described in claim 1. 20. A coated product comprising a substrate as a shaped body, wherein one surface, both surfaces or the entire surface of the substrate is coated with the electrically conducting composition described in claim 12. 21. The coated product as claimed in claim 19, wherein the substrate is a silicon wafer. 22. The coated product as claimed in claim 19, wherein the substrate is entirely or partially coated with indium tin oxide. 23. An electronic device comprising the self-doping type electrically conducting polymer described in claim 1. 24. An electronic device comprising the electrically conducting composition described in claim 12. 25. An organic light-emitting element comprising at least one light-emitting layer between a pair of anode and cathode, wherein the self-doping type electrically conducting polymer described in claim 1 is contained in the anode buffer layer. 26. The organic light-emitting element as claimed in claim 25, wherein the self-doping type electrically conducting polymer has a sulfonic acid group. 27. The organic light-emitting element as claimed in claim 25, wherein the self-doping type electrically conducting polymers are crosslinked through a sulfone bond. 28. An organic light-emitting element comprising the self-doping type electrically conducting polymer described in claim 1. 29. An organic light-emitting element comprising the electrically conducting composition described in claim 12. 30. The organic light-emitting element as claimed in claim 25, wherein the light-emitting layer comprises a fluorescence-emitting polymer material. 31. The organic light-emitting element as claimed in 25, wherein the light-emitting layer comprises a phosphorescence-emitting polymer material. 32. An organic EL display comprising the organic light-emitting element described in claim 25. 33. A display device for portable terminals, comprising the organic EL display described in claim 32.
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이 특허에 인용된 특허 (7)
Rauchschwalbe, Günter; Klausener, Alexander; Kirchmeyer, Stephan; Reuter, Knud, Benzodioxinothiophenes, their preparation and use.
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