CN102449023B - 多环联噻吩 - Google Patents
多环联噻吩 Download PDFInfo
- Publication number
- CN102449023B CN102449023B CN201080023293.5A CN201080023293A CN102449023B CN 102449023 B CN102449023 B CN 102449023B CN 201080023293 A CN201080023293 A CN 201080023293A CN 102449023 B CN102449023 B CN 102449023B
- Authority
- CN
- China
- Prior art keywords
- alkyl
- group
- aryl
- independently
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 0 C*(*)**(C)c([s]c1c2[s]c(*)c(*)c2c2N=C(*)IC)c(*)c1c2I Chemical compound C*(*)**(C)c([s]c1c2[s]c(*)c(*)c2c2N=C(*)IC)c(*)c1c2I 0.000 description 3
- SEEYREPSKCQBBF-UHFFFAOYSA-N CN(C(C=C1)=O)C1=O Chemical compound CN(C(C=C1)=O)C1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- KYEACNNYFNZCST-UHFFFAOYSA-N CN(C(CC1)=O)C1=O Chemical compound CN(C(CC1)=O)C1=O KYEACNNYFNZCST-UHFFFAOYSA-N 0.000 description 1
- ZXLYYQUMYFHCLQ-UHFFFAOYSA-N CN(C(c1c2cccc1)=O)C2=O Chemical compound CN(C(c1c2cccc1)=O)C2=O ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 0.000 description 1
- INDQUNWDQCVHJU-UHFFFAOYSA-N CN(Cc1c-2[s]cc1)Cc1c-2[s]cc1 Chemical compound CN(Cc1c-2[s]cc1)Cc1c-2[s]cc1 INDQUNWDQCVHJU-UHFFFAOYSA-N 0.000 description 1
- IVLHQJWDERVGTG-UHFFFAOYSA-N C[Si+](C)(C)c([s]c1c(c(C=N)c2nc3-c4ccc(C=O)cc4)S)cc1c2[n]3-c1ccccc1 Chemical compound C[Si+](C)(C)c([s]c1c(c(C=N)c2nc3-c4ccc(C=O)cc4)S)cc1c2[n]3-c1ccccc1 IVLHQJWDERVGTG-UHFFFAOYSA-N 0.000 description 1
- WVQBMJNQBZCKCW-UHFFFAOYSA-N C[Si+](C)(C)c([s]c1c2[s]c([S+](C)C)cc2c23)cc1c2nc(-c1ccc(C=C)cc1)[n]3-c1ccccc1 Chemical compound C[Si+](C)(C)c([s]c1c2[s]c([S+](C)C)cc2c23)cc1c2nc(-c1ccc(C=C)cc1)[n]3-c1ccccc1 WVQBMJNQBZCKCW-UHFFFAOYSA-N 0.000 description 1
- YZEKNUVKFQGRAL-UHFFFAOYSA-N C[Si+](C)(C)c([s]c1c2[s]c([S+](C)C)cc2c23)cc1c2nc(-c1ccc(C=O)cc1)[n]3-c1ccccc1 Chemical compound C[Si+](C)(C)c([s]c1c2[s]c([S+](C)C)cc2c23)cc1c2nc(-c1ccc(C=O)cc1)[n]3-c1ccccc1 YZEKNUVKFQGRAL-UHFFFAOYSA-N 0.000 description 1
- NEJWVWWBJMYCEH-UHFFFAOYSA-N C[Si+](C)(C)c([s]c1c2[s]c([Si+](C)(C)C)cc2c2nc3-c(cc4)ccc4Br)cc1c2[n]3-c1ccccc1 Chemical compound C[Si+](C)(C)c([s]c1c2[s]c([Si+](C)(C)C)cc2c2nc3-c(cc4)ccc4Br)cc1c2[n]3-c1ccccc1 NEJWVWWBJMYCEH-UHFFFAOYSA-N 0.000 description 1
- AFOLLEYUBTWQBH-RFTYBOQRSA-O C[Si+](C)(C)c1cc(/C(/C(/c2c-3[s]c([S+](C)C)c2)=N\O)=N\O)c-3[s]1 Chemical compound C[Si+](C)(C)c1cc(/C(/C(/c2c-3[s]c([S+](C)C)c2)=N\O)=N\O)c-3[s]1 AFOLLEYUBTWQBH-RFTYBOQRSA-O 0.000 description 1
- ANKMJHHGWKARLY-UHFFFAOYSA-N C[Si+](C)(C)c1cc(C(C(c2c-3[s]c([S+](C)C)c2)=O)=O)c-3[s]1 Chemical compound C[Si+](C)(C)c1cc(C(C(c2c-3[s]c([S+](C)C)c2)=O)=O)c-3[s]1 ANKMJHHGWKARLY-UHFFFAOYSA-N 0.000 description 1
- KCEPXHKNQHSBMO-UHFFFAOYSA-N C[Si+](C)(C)c1cc(C(N(c2ccc(C=C)cc2)C(c2c-3[s]c([Si+](C)(C)C)c2)=O)=O)c-3[s]1 Chemical compound C[Si+](C)(C)c1cc(C(N(c2ccc(C=C)cc2)C(c2c-3[s]c([Si+](C)(C)C)c2)=O)=O)c-3[s]1 KCEPXHKNQHSBMO-UHFFFAOYSA-N 0.000 description 1
- XSYNYVKODSFIRL-UHFFFAOYSA-N C[Si+](C)(C)c1cc(C(NC(c2c-3[s]c([Si+](C)(C)C)c2)=O)=O)c-3[s]1 Chemical compound C[Si+](C)(C)c1cc(C(NC(c2c-3[s]c([Si+](C)(C)C)c2)=O)=O)c-3[s]1 XSYNYVKODSFIRL-UHFFFAOYSA-N 0.000 description 1
- JJRJMAFDVUFYOF-UHFFFAOYSA-N C[Si+](C)(C)c1cc2c3nc(c4c(c5c6cc([Si+](C)(C)C)[s]5)[s]c([S+](C)C)c4)c6nc3c(cc([s]3)[S+](C)C)c3c2[s]1 Chemical compound C[Si+](C)(C)c1cc2c3nc(c4c(c5c6cc([Si+](C)(C)C)[s]5)[s]c([S+](C)C)c4)c6nc3c(cc([s]3)[S+](C)C)c3c2[s]1 JJRJMAFDVUFYOF-UHFFFAOYSA-N 0.000 description 1
- WWBHOBFOGWENFK-UHFFFAOYSA-N Nc1c(cc[s]2)c2c2[s]ccc2c1N Chemical compound Nc1c(cc[s]2)c2c2[s]ccc2c1N WWBHOBFOGWENFK-UHFFFAOYSA-N 0.000 description 1
- YLKKIBOMGQAGGA-UHFFFAOYSA-N c1c[s]c2c1c1n[s]nc1c1c2[s]cc1 Chemical compound c1c[s]c2c1c1n[s]nc1c1c2[s]cc1 YLKKIBOMGQAGGA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F128/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
- C08F128/06—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur by a heterocyclic ring containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/06—Polythioethers from cyclic thioethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/32—Polythiazoles; Polythiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/008—Dyes containing a substituent, which contains a silicium atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10D—INORGANIC ELECTRIC SEMICONDUCTOR DEVICES
- H10D30/00—Field-effect transistors [FET]
- H10D30/60—Insulated-gate field-effect transistors [IGFET]
- H10D30/67—Thin-film transistors [TFT]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
- H10F10/00—Individual photovoltaic cells, e.g. solar cells
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3247—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing combinations of different heteroatoms other than nitrogen and oxygen or nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/414—Stille reactions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/91—Photovoltaic applications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/92—TFT applications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/95—Use in organic luminescent diodes
-
- 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
-
- 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]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
-
- 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
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Chemical & Material Sciences (AREA)
- Optics & Photonics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Thin Film Transistor (AREA)
- Photovoltaic Devices (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09161243 | 2009-05-27 | ||
| EP09161243.2 | 2009-05-27 | ||
| EP09170185 | 2009-09-14 | ||
| EP09170185.4 | 2009-09-14 | ||
| PCT/EP2010/057038 WO2010136401A2 (en) | 2009-05-27 | 2010-05-21 | Polycyclic dithiophenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102449023A CN102449023A (zh) | 2012-05-09 |
| CN102449023B true CN102449023B (zh) | 2015-10-07 |
Family
ID=42309549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201080023293.5A Expired - Fee Related CN102449023B (zh) | 2009-05-27 | 2010-05-21 | 多环联噻吩 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US9233930B2 (enExample) |
| EP (1) | EP2435497B1 (enExample) |
| JP (1) | JP5886190B2 (enExample) |
| KR (1) | KR101805203B1 (enExample) |
| CN (1) | CN102449023B (enExample) |
| WO (1) | WO2010136401A2 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8859714B1 (en) | 2009-07-01 | 2014-10-14 | Northwestern University | Polymeric semiconductors and related devices |
| US8946688B2 (en) * | 2009-12-14 | 2015-02-03 | Idemitsu Kosan Co., Ltd. | Polycyclic ring-fused compound and organic thin film transistor utilizing the same |
| US8895693B2 (en) | 2010-06-25 | 2014-11-25 | Samsung Electronics Co., Ltd. | Electron-donating polymers and organic solar cells including the same |
| WO2012083510A1 (zh) * | 2010-12-20 | 2012-06-28 | 海洋王照明科技股份有限公司 | 有机半导体材料及其制备方法和应用 |
| JP2012162514A (ja) * | 2011-01-20 | 2012-08-30 | Kuraray Co Ltd | ジチエノゲルモール重合体及びそれを含有した有機半導体デバイス |
| US9748496B2 (en) | 2011-02-02 | 2017-08-29 | Idemitsu Kosan Co., Ltd. | Nitrogenated heterocyclic derivative, electron-transporting material for organic electroluminescent elements, and organic electroluminescent element using same |
| GB201105482D0 (en) * | 2011-03-31 | 2011-05-18 | Imp Innovations Ltd | Polymers |
| WO2012146504A1 (en) * | 2011-04-27 | 2012-11-01 | Basf Se | Semiconductor materials based on dithienopyridone copolymers |
| KR101853395B1 (ko) | 2011-05-23 | 2018-04-30 | 삼성전자주식회사 | 전자 공여체 고분자 및 이를 포함하는 태양 전지 |
| US10316135B2 (en) * | 2011-06-17 | 2019-06-11 | The Regents Of The University Of California | Fluorine substitution influence on benzo[2,1,3]thiodiazole based polymers for field-effect transistor applications |
| KR101777326B1 (ko) | 2011-10-05 | 2017-09-12 | 삼성전자주식회사 | 전자 공여체 고분자 및 이를 포함하는 유기 태양 전지 |
| CN103917575A (zh) | 2011-11-02 | 2014-07-09 | 三菱化学株式会社 | 共轭高分子的制造方法、共轭高分子、光电转换元件、太阳能电池以及太阳能电池模块 |
| JP6040939B2 (ja) | 2011-11-02 | 2016-12-07 | 三菱化学株式会社 | 縮合多環芳香族化合物の製造方法及び共役高分子 |
| US8835598B2 (en) * | 2012-03-22 | 2014-09-16 | Polyera Corporation | Conjugated polymers and their use in optoelectronic devices |
| KR101424978B1 (ko) * | 2012-05-24 | 2014-07-31 | 경상대학교산학협력단 | 길만시약 화합물을 이용한 헤테로 융합고리 화합물의 신규한 제조방법 |
| US9359470B2 (en) | 2012-07-23 | 2016-06-07 | Basf Se | Dithienobenzofuran polymers and small molecules for electronic application |
| EP2928940B1 (en) | 2012-12-04 | 2021-03-03 | CLAP Co., Ltd. | Functionalized benzodithiophene polymers for electronic application |
| US9472764B2 (en) * | 2012-12-04 | 2016-10-18 | Northwestern University | Conjugated polymers and their use in optoelectronic devices |
| JP6112717B2 (ja) * | 2013-05-13 | 2017-04-12 | 国立大学法人東京工業大学 | ジチエノゲルモール骨格を有する有機ヘテロ高分子およびその製造方法 |
| CA2953681A1 (en) * | 2013-06-28 | 2015-04-02 | Solarwindow Technologies, Inc. | Preparation and coating of pilot equipment with organic photovoltaic films to produce electricity for emergency power supply systems for pilots |
| JP6184234B2 (ja) * | 2013-08-02 | 2017-08-23 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料 |
| CN103601740B (zh) * | 2013-09-17 | 2016-02-24 | 武汉工程大学 | 一种2,1,3-苯并噻二唑并二噻吩衍生溴代物及其合成方法 |
| JP6209099B2 (ja) * | 2014-02-10 | 2017-10-04 | 富士フイルム株式会社 | 光電変換素子およびその使用方法、光センサ、撮像素子、化合物およびその製造方法 |
| KR20170056600A (ko) | 2014-09-09 | 2017-05-23 | 메르크 파텐트 게엠베하 | 공액 중합체 |
| US10875957B2 (en) * | 2015-11-11 | 2020-12-29 | The Regents Of The University Of California | Fluorine substitution influence on benzo[2,1,3]thiodiazole based polymers for field-effect transistor applications |
| CN105906788B (zh) * | 2016-06-12 | 2018-06-29 | 南京邮电大学 | 含有吩嗪结构的聚合物及其制备方法和应用 |
| JP6676181B2 (ja) * | 2016-09-29 | 2020-04-08 | 富士フイルム株式会社 | 微結晶有機半導体膜、有機半導体トランジスタ、及び有機半導体トランジスタの製造方法 |
| US10312444B2 (en) | 2016-10-06 | 2019-06-04 | International Business Machines Corporation | Organic semiconductors with dithienofuran core monomers |
| CN106967096B (zh) * | 2017-05-17 | 2019-01-29 | 中节能万润股份有限公司 | 一种含噻吩结构的二唑类杂环化合物及其应用 |
| US20210009604A1 (en) * | 2018-05-07 | 2021-01-14 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd | Bifuran-imide-based materials and uses thereof |
| US11332579B1 (en) | 2021-11-19 | 2022-05-17 | Phillips 66 Company | Fused dithieno benzothiadiazole polymers for organic photovoltaics |
| US11849629B2 (en) | 2021-11-19 | 2023-12-19 | Phillips 66 Company | Fused dithieno benzothiadiazole polymers for organic photovolatics |
| US11326019B1 (en) | 2021-11-19 | 2022-05-10 | Phillips 66 Company | Fused dithieno benzothiadiazole polymers for organic photovoltaics |
| US11690283B2 (en) | 2021-11-19 | 2023-06-27 | Phillips 66 Company | Fused dithieno benzothiadiazole polymers for organic photovoltaics |
| CN114349766B (zh) * | 2021-12-20 | 2023-04-07 | 淮阴工学院 | 一种d-a-d型有机半导体材料及其制备方法和应用 |
| CN114507337A (zh) * | 2022-02-21 | 2022-05-17 | 东华大学 | 含有喹喔啉结构的共轭聚合物及其合成方法与应用 |
| CN115724873B (zh) * | 2022-11-01 | 2025-10-28 | 汕头大学 | 基于苯并二噻吩的稠环单体、其聚合物及制备方法和应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003052841A1 (en) * | 2001-12-19 | 2003-06-26 | Avecia Limited | Organic field effect transistor with an organic dielectric |
| WO2005003126A1 (en) * | 2003-07-07 | 2005-01-13 | The University Of Hong Kong | Photochromic diarylethene-containing coordination compounds and the production thereof |
| EP2006291A1 (en) * | 2006-03-10 | 2008-12-24 | Osaka University | Fused ring compound and method for producing same, polymer, organic thin film containing those, and organic thin film device and organic thin film transistor comprising such organic thin film |
| WO2009115413A2 (en) * | 2008-03-17 | 2009-09-24 | Basf Se | Substituted oligo- or polythiophenes |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2339128T3 (es) * | 2004-03-04 | 2010-05-17 | The Procter And Gamble Company | Composiones cosmeticas para teñir el cabello que los contienen y uso de las mismas. |
| KR101546985B1 (ko) | 2007-10-09 | 2015-08-24 | 바스프 에스이 | 피롤로피롤 유도체, 그의 제조 및 용도 |
| EP2205657B1 (en) | 2007-10-25 | 2017-04-05 | Basf Se | Ketopyrroles as organic semiconductors |
| WO2009092671A2 (en) | 2008-01-25 | 2009-07-30 | Basf Se | Organic light emitting systems |
| JP5535208B2 (ja) | 2008-07-18 | 2014-07-02 | ビーエーエスエフ ソシエタス・ヨーロピア | 電子用途のためのアザピレン |
| WO2010046259A1 (en) | 2008-10-21 | 2010-04-29 | Basf Se | Polycyclic compounds for electronic applications |
| CN102272192B (zh) | 2008-10-31 | 2016-12-07 | 巴斯夫欧洲公司 | 用于有机场效应晶体管的二酮吡咯并吡咯聚合物 |
| CN102203160B (zh) | 2008-10-31 | 2013-07-17 | 巴斯夫欧洲公司 | 用于有机半导体器件的二酮吡咯并吡咯聚合物 |
| JP5675787B2 (ja) * | 2009-05-27 | 2015-02-25 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 有機半導体装置で使用するためのジケトピロロピロールポリマー |
| JP5763632B2 (ja) | 2009-06-30 | 2015-08-12 | ソルベイ ユーエスエイ インコーポレイテッド | 少なくとも1つのビチオフェン繰り返し単位を含むポリマー、該ポリマーを合成する方法、およびそれを含む組成物 |
| US20110006287A1 (en) * | 2009-07-10 | 2011-01-13 | Wei You | Polymers with tunable band gaps for photonic and electronic applications |
| US8624232B2 (en) * | 2009-08-28 | 2014-01-07 | Prashant Sonar | Ambipolar polymeric semiconductor materials and organic electronic devices |
-
2010
- 2010-05-21 EP EP10723972.5A patent/EP2435497B1/en active Active
- 2010-05-21 KR KR1020117031222A patent/KR101805203B1/ko not_active Expired - Fee Related
- 2010-05-21 JP JP2012512320A patent/JP5886190B2/ja not_active Expired - Fee Related
- 2010-05-21 CN CN201080023293.5A patent/CN102449023B/zh not_active Expired - Fee Related
- 2010-05-21 US US13/322,506 patent/US9233930B2/en active Active
- 2010-05-21 WO PCT/EP2010/057038 patent/WO2010136401A2/en not_active Ceased
-
2015
- 2015-12-10 US US14/965,128 patent/US9716241B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003052841A1 (en) * | 2001-12-19 | 2003-06-26 | Avecia Limited | Organic field effect transistor with an organic dielectric |
| WO2005003126A1 (en) * | 2003-07-07 | 2005-01-13 | The University Of Hong Kong | Photochromic diarylethene-containing coordination compounds and the production thereof |
| EP2006291A1 (en) * | 2006-03-10 | 2008-12-24 | Osaka University | Fused ring compound and method for producing same, polymer, organic thin film containing those, and organic thin film device and organic thin film transistor comprising such organic thin film |
| WO2009115413A2 (en) * | 2008-03-17 | 2009-09-24 | Basf Se | Substituted oligo- or polythiophenes |
Non-Patent Citations (4)
| Title |
|---|
| "Highly conjugated acrylate-functionalized polythiophenes from anodic coupling of thiophene- and bithiophene-hexyl acrylates";G.Zotti,et al;《Synthetic Metals》;19990830;第105卷(第2期);第135–139页 * |
| "Synthesis of oligomers having a pendant dithienosilole unit and their applications to EL device materials";Kwang-Hoi Lee,et al;《Journal of Organometallic Chemistry》;20050117;第690卷(第2期);第333-337页 * |
| Joseph A. Letizia,et al."n-Channel Polymers by Design:Optimizing the Interplay of Solubilizing Substituents,Crystal Packing,and Field-Effect Transistor Characteristics in Polymeric Bithiophene-Imide Semiconductors".《J. Am. Chem. Soc.》.2008,第130卷(第30期),第9679-9694页. * |
| Thomas Baumgartner,et al."The Dithieno[3,2-b:2’,3’-d]phosphole System:A Novel Building Block for Highly Luminescent π-Conjugated Materials".《Angewandte Chemie International Edition》.2004,第43卷(第45期),第6197-6201页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010136401A3 (en) | 2011-08-04 |
| KR101805203B1 (ko) | 2018-01-10 |
| KR20120030113A (ko) | 2012-03-27 |
| CN102449023A (zh) | 2012-05-09 |
| US9233930B2 (en) | 2016-01-12 |
| US20160104849A1 (en) | 2016-04-14 |
| US20120097935A1 (en) | 2012-04-26 |
| JP5886190B2 (ja) | 2016-03-16 |
| JP2012528100A (ja) | 2012-11-12 |
| WO2010136401A4 (en) | 2011-11-10 |
| WO2010136401A2 (en) | 2010-12-02 |
| EP2435497B1 (en) | 2023-07-05 |
| EP2435497A2 (en) | 2012-04-04 |
| US9716241B2 (en) | 2017-07-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102449023B (zh) | 多环联噻吩 | |
| KR101555076B1 (ko) | 치환된 올리고- 또는 폴리티오펜 | |
| CN102449030B (zh) | 用于有机半导体器件中的二酮基吡咯并吡咯聚合物 | |
| CN101835821B (zh) | 作为有机半导体的酮基吡咯 | |
| JP5635070B2 (ja) | 有機半導体デバイスでの使用のためのジケトピロロピロールポリマー | |
| JP5787876B2 (ja) | ピロロピロール誘導体、その製造方法及び半導体としての使用 | |
| US20110317628A1 (en) | Method of performing wireless communication in multi-carrier system | |
| CN104334610A (zh) | 二酮基吡咯并吡咯聚合物和小分子 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20200904 Address after: Seoul, South Kerean Patentee after: Clap Ltd. Address before: Ludwigshafen, Germany Patentee before: BASF SE |
|
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20151007 |