KR20120022897A - 탈할로겐화 - Google Patents
탈할로겐화 Download PDFInfo
- Publication number
- KR20120022897A KR20120022897A KR20117026681A KR20117026681A KR20120022897A KR 20120022897 A KR20120022897 A KR 20120022897A KR 20117026681 A KR20117026681 A KR 20117026681A KR 20117026681 A KR20117026681 A KR 20117026681A KR 20120022897 A KR20120022897 A KR 20120022897A
- Authority
- KR
- South Korea
- Prior art keywords
- dehalogenation
- polythiophene
- composition
- polymer
- prepared
- 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.)
- Withdrawn
Links
- 238000005695 dehalogenation reaction Methods 0.000 title claims abstract description 69
- 229920000642 polymer Polymers 0.000 claims abstract description 86
- 229920000123 polythiophene Polymers 0.000 claims abstract description 66
- 239000000463 material Substances 0.000 claims abstract description 14
- 238000013086 organic photovoltaic Methods 0.000 claims abstract description 5
- 238000007256 debromination reaction Methods 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 34
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 239000011777 magnesium Substances 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 230000005525 hole transport Effects 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 239000012190 activator Substances 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 4
- 239000007818 Grignard reagent Substances 0.000 claims description 3
- 238000000732 glass refractive index measurement Methods 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 238000010626 work up procedure Methods 0.000 claims description 3
- 238000006880 cross-coupling reaction Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000001879 gelation Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000007868 post-polymerization treatment Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 41
- -1 poly (p-phenylene) Polymers 0.000 description 32
- 229920000547 conjugated polymer Polymers 0.000 description 30
- 125000001424 substituent group Chemical group 0.000 description 23
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 239000002019 doping agent Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920001940 conductive polymer Polymers 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 125000000732 arylene group Chemical group 0.000 description 8
- 229920001400 block copolymer Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229930192474 thiophene Natural products 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000976 ink Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- DBTNVRCCIDISMV-UHFFFAOYSA-L lithium;magnesium;propane;dichloride Chemical compound [Li+].[Mg+2].[Cl-].[Cl-].C[CH-]C DBTNVRCCIDISMV-UHFFFAOYSA-L 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000005529 alkyleneoxy group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000000025 interference lithography Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
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- 238000005259 measurement Methods 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- UCUFJCROAFAXJH-UHFFFAOYSA-N 2,5-dibromo-3,4-bis[2-(2-butoxyethoxy)ethoxy]thiophene Chemical compound CCCCOCCOCCOC1=C(Br)SC(Br)=C1OCCOCCOCCCC UCUFJCROAFAXJH-UHFFFAOYSA-N 0.000 description 2
- LIKJXMCWVFSNHW-UHFFFAOYSA-N 3,4-bis[2-(2-butoxyethoxy)ethoxy]thiophene Chemical compound CCCCOCCOCCOC1=CSC=C1OCCOCCOCCCC LIKJXMCWVFSNHW-UHFFFAOYSA-N 0.000 description 2
- LHYNYTDUZMSYNO-UHFFFAOYSA-N 3-[2-(2-methoxyethoxy)ethoxy]thiophene Chemical compound COCCOCCOC=1C=CSC=1 LHYNYTDUZMSYNO-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 229920000292 Polyquinoline Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003990 capacitor Substances 0.000 description 2
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- 238000012512 characterization method Methods 0.000 description 2
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- 239000008367 deionised water Substances 0.000 description 2
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- OJKYLADXDAXTSO-UHFFFAOYSA-N 1-(4-thieno[3,4-c]pyridin-1-ylphenyl)thieno[3,4-c]pyridine Chemical compound C1=CN=CC2=CSC(C=3C=CC(=CC=3)C3=C4C=CN=CC4=CS3)=C21 OJKYLADXDAXTSO-UHFFFAOYSA-N 0.000 description 1
- IDQBJILTOGBZCR-UHFFFAOYSA-N 1-butoxypropan-1-ol Chemical compound CCCCOC(O)CC IDQBJILTOGBZCR-UHFFFAOYSA-N 0.000 description 1
- DSMILXZNXVAKBW-UHFFFAOYSA-N 2,5-dibromo-3,4-bis[2-(2-butoxybutoxy)butoxy]thiophene Chemical compound CCCCOC(CC)COC(CC)COC1=C(Br)SC(Br)=C1OCC(CC)OCC(CC)OCCCC DSMILXZNXVAKBW-UHFFFAOYSA-N 0.000 description 1
- DVEJEMGEFAIYTC-UHFFFAOYSA-N 2,5-dibromo-3,4-bis[2-(2-ethoxyethoxy)ethoxy]thiophene Chemical compound CCOCCOCCOC1=C(Br)SC(Br)=C1OCCOCCOCC DVEJEMGEFAIYTC-UHFFFAOYSA-N 0.000 description 1
- RZJKCMRAHRQAJL-UHFFFAOYSA-N 2,5-dibromo-3,4-bis[2-(2-methoxyethoxy)ethoxy]thiophene Chemical compound COCCOCCOC1=C(Br)SC(Br)=C1OCCOCCOC RZJKCMRAHRQAJL-UHFFFAOYSA-N 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 1
- RYEXTBOQKFUPOE-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].CC[CH2-] RYEXTBOQKFUPOE-UHFFFAOYSA-M 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920003252 rigid-rod polymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000007847 structural defect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 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
- 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
-
- 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
-
- 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
- H10K71/311—Purifying organic semiconductor materials
-
- 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
- H10K99/00—Subject matter not provided for in other groups of this subclass
-
- 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
-
- 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]
- Y10T428/31533—Of polythioether
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16847009P | 2009-04-10 | 2009-04-10 | |
| US61/168,470 | 2009-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20120022897A true KR20120022897A (ko) | 2012-03-12 |
Family
ID=42244521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR20117026681A Withdrawn KR20120022897A (ko) | 2009-04-10 | 2010-04-09 | 탈할로겐화 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20100273007A1 (enExample) |
| EP (1) | EP2417178A1 (enExample) |
| JP (1) | JP2012523483A (enExample) |
| KR (1) | KR20120022897A (enExample) |
| WO (1) | WO2010118370A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107068914B (zh) | 2010-07-02 | 2020-05-08 | 日产化学工业株式会社 | 空穴传输组合物及相关器件和方法(i) |
| WO2012136781A1 (en) | 2011-04-05 | 2012-10-11 | Acreo Ab | Colloid electrolyte composition |
| TWI555772B (zh) | 2011-10-21 | 2016-11-01 | 索爾維美國有限公司 | 經由氧化聚合之共軛聚合物之改良合成法及相關組合物 |
| HK1208764A1 (en) | 2012-05-15 | 2016-03-11 | Nissan Chemical Industries, Ltd. | Hole transport materials including oled applications |
| CN103936972A (zh) * | 2014-04-14 | 2014-07-23 | 东南大学 | 一种全共轭嵌段共聚物及其制备方法 |
| CN107849377A (zh) * | 2015-07-17 | 2018-03-27 | 日产化学工业株式会社 | 适用于有机电子的包含准金属纳米颗粒的非水性油墨组合物 |
| CN114105746B (zh) * | 2021-11-24 | 2023-08-01 | 温州大学 | 一种光催化α-卤代羰基化合物的还原脱卤方法 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4356429A (en) | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
| DE3107245A1 (de) | 1981-02-26 | 1982-09-09 | Basf Ag, 6700 Ludwigshafen | Gleitmittel fuer die formgebende verarbeitung von chlorhaltigen thermoplasten, die als wirksames prinzip veresterte ethylen-acrylsaeure-copolymerisate enthalten |
| US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
| US4737557A (en) | 1986-03-20 | 1988-04-12 | Agency Of Industrial Science And Technology | 3-N-higher alkylthiophene polymer and composition thereof |
| FR2596566B1 (fr) * | 1986-04-01 | 1989-03-10 | Solvay | Polymeres conducteurs derives de 3-alkylthiophenes, procede pour leur fabrication et dispositifs electroconducteurs les contenant |
| GB8909011D0 (en) * | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| US5047687A (en) | 1990-07-26 | 1991-09-10 | Eastman Kodak Company | Organic electroluminescent device with stabilized cathode |
| GB9018698D0 (en) | 1990-08-24 | 1990-10-10 | Lynxvale Ltd | Semiconductive copolymers for use in electroluminescent devices |
| US5331183A (en) * | 1992-08-17 | 1994-07-19 | The Regents Of The University Of California | Conjugated polymer - acceptor heterojunctions; diodes, photodiodes, and photovoltaic cells |
| US6166172A (en) | 1999-02-10 | 2000-12-26 | Carnegie Mellon University | Method of forming poly-(3-substituted) thiophenes |
| AT411306B (de) | 2000-04-27 | 2003-11-25 | Qsel Quantum Solar Energy Linz | Photovoltaische zelle mit einer photoaktiven schicht aus zwei molekularen organischen komponenten |
| AT410729B (de) | 2000-04-27 | 2003-07-25 | Qsel Quantum Solar Energy Linz | Photovoltaische zelle mit einer photoaktiven schicht aus zwei molekularen organischen komponenten |
| US6602974B1 (en) * | 2001-12-04 | 2003-08-05 | Carnegie Mellon University | Polythiophenes, block copolymers made therefrom, and methods of forming the same |
| DE602004016858D1 (de) * | 2003-08-06 | 2008-11-13 | Merck Patent Gmbh | Verfahren zur herstellung von regioregulären polymeren |
| KR101120303B1 (ko) * | 2003-08-06 | 2012-03-07 | 메르크 파텐트 게엠베하 | 위치규칙적인 중합체의 제조방법 |
| US7288329B2 (en) * | 2004-02-25 | 2007-10-30 | Eastman Kodak Company | Electroluminescent devices including conjugated polymers containing an azole structure |
| US7368624B2 (en) | 2004-03-30 | 2008-05-06 | Eastman Kodak Company | Synthesis for polycyclic aromatic hydrocarbon compounds |
| EP1582523A1 (en) * | 2004-04-02 | 2005-10-05 | Ludwig-Maximilians-Universität München | Method of preparing organomagnesium compounds |
| CN100583485C (zh) | 2004-09-24 | 2010-01-20 | 普莱克斯托尼克斯公司 | 含杂原子立体规则性聚（3-取代噻吩）的光电池 |
| KR20070106716A (ko) * | 2005-02-11 | 2007-11-05 | 메르크 파텐트 게엠베하 | 위치 규칙성 중합체의 제조 방법 |
| US8754175B2 (en) * | 2005-03-16 | 2014-06-17 | Carnegie Mellon University | Monocapped conductive polymers with alkenyl or alkynyl end groups and block copolymers therefrom |
| JP5009516B2 (ja) * | 2005-09-14 | 2012-08-22 | 出光興産株式会社 | 芳香族化合物の製造方法及びその方法で得られた芳香族化合物 |
| CN103227289B (zh) | 2006-06-13 | 2016-08-17 | 索尔维美国有限公司 | 包含富勒烯及其衍生物的有机光伏器件 |
| CN101563388B (zh) * | 2006-07-21 | 2013-05-15 | 普莱克斯托尼克斯公司 | 导电聚合物的磺化和oled器件、光电器件以及esd器件 |
| JP2010502791A (ja) * | 2006-09-01 | 2010-01-28 | カーネギー メロン ユニバーシティ | ユニバーサルグリニャールメタセシス重合 |
| US7838624B2 (en) * | 2007-05-15 | 2010-11-23 | Plextronics, Inc. | Mixed halogen polymerization |
| EP2276788B1 (en) * | 2008-04-11 | 2014-08-27 | Plextronics, Inc. | Doped conjugated polymers, devices, and methods of making devices |
| CN101376686A (zh) * | 2008-09-28 | 2009-03-04 | 南京邮电大学 | 本体异质结太阳电池聚合物给体材料及合成和应用方法 |
| US11923908B2 (en) | 2021-03-19 | 2024-03-05 | The Trustees Of The University Of Pennsylvania | Integrated coherent receiver with off PLL bandwidth demodulation |
-
2010
- 2010-04-09 EP EP10714141A patent/EP2417178A1/en not_active Withdrawn
- 2010-04-09 WO PCT/US2010/030601 patent/WO2010118370A1/en not_active Ceased
- 2010-04-09 JP JP2012504899A patent/JP2012523483A/ja active Pending
- 2010-04-09 KR KR20117026681A patent/KR20120022897A/ko not_active Withdrawn
- 2010-04-09 US US12/757,814 patent/US20100273007A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2417178A1 (en) | 2012-02-15 |
| JP2012523483A (ja) | 2012-10-04 |
| US20100273007A1 (en) | 2010-10-28 |
| WO2010118370A1 (en) | 2010-10-14 |
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