CA2625306A1 - Oligothiophenes regioreguliers a noyau d'accepteurs d'electrons, utilises comme elements constitutifs de polymeres conjugues solubles a faible energie interbande - Google Patents

Oligothiophenes regioreguliers a noyau d'accepteurs d'electrons, utilises comme elements constitutifs de polymeres conjugues solubles a faible energie interbande Download PDF

Info

Publication number: CA2625306A1
Authority: CA; Canada
Prior art keywords: alkyl group; electron; regioregular; cored; formula
Prior art date: 2008-03-11
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.): Abandoned

Application number

CA002625306A

Other languages

English (en)

Inventor

Jianping Lu

Jianfu Ding

Fushun Liang

Nicolas Drolet

Ye Tao

Raluca Movileanu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

National Research Council of Canada

Original Assignee

National Research Council of Canada

Priority date (The priority date 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 date listed.)

2008-03-11

Filing date

2008-03-11

Publication date

2009-09-11

2008-03-11 Application filed by National Research Council of Canada filed Critical National Research Council of Canada

2008-03-11 Priority to CA002625306A priority Critical patent/CA2625306A1/fr

2009-09-11 Publication of CA2625306A1 publication Critical patent/CA2625306A1/fr

Status Abandoned legal-status Critical Current

Links

229920000547 conjugated polymer Polymers 0.000 title claims description 7
230000005669 field effect Effects 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 26
229920000642 polymer Polymers 0.000 claims description 22
238000000034 method Methods 0.000 claims description 18
238000013459 approach Methods 0.000 claims description 12
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
-1 2-ethylhexyl Chemical group 0.000 claims description 11
239000000370 acceptor Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 6
FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical group C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims description 5
239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
125000006575 electron-withdrawing group Chemical group 0.000 claims description 5
VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 5
229960005544 indolocarbazole Drugs 0.000 claims description 5
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
238000006619 Stille reaction Methods 0.000 claims description 3
238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
230000002194 synthesizing effect Effects 0.000 claims 5
239000000463 material Substances 0.000 abstract description 19
150000001875 compounds Chemical class 0.000 abstract description 7
238000007334 copolymerization reaction Methods 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000004065 semiconductor Substances 0.000 description 10
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000010410 layer Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 7
238000000113 differential scanning calorimetry Methods 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000758 substrate Substances 0.000 description 6
NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 5
230000037230 mobility Effects 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002800 charge carrier Substances 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000000178 monomer Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 3
230000008569 process Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
OZNXIGFAKCITRZ-UHFFFAOYSA-N (4-hexylthiophen-2-yl)-trimethylstannane Chemical compound CCCCCCC1=CSC([Sn](C)(C)C)=C1 OZNXIGFAKCITRZ-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
MBDZHPMISHRUFG-UHFFFAOYSA-N 4,7-bis[4-octyl-5-(4-octylthiophen-2-yl)thiophen-2-yl]-2,1,3-benzothiadiazole Chemical compound C(CCCCCCC)C1=C(SC(=C1)C1=CC=C(C2=NSN=C21)C2=CC(=C(S2)C=2SC=C(C2)CCCCCCCC)CCCCCCCC)C=2SC=C(C2)CCCCCCCC MBDZHPMISHRUFG-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000001938 differential scanning calorimetry curve Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
229920002457 flexible plastic Polymers 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000003993 interaction Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
DOHOHOKWNWTQLM-UHFFFAOYSA-N 4,7-bis(4-octylthiophen-2-yl)-2,1,3-benzothiadiazole Chemical compound CCCCCCCCC1=CSC(C=2C3=NSN=C3C(C=3SC=C(CCCCCCCC)C=3)=CC=2)=C1 DOHOHOKWNWTQLM-UHFFFAOYSA-N 0.000 description 1
AMYLTENEOQNKGO-UHFFFAOYSA-N 4,7-bis(5-bromo-4-octylthiophen-2-yl)-2,1,3-benzothiadiazole Chemical compound S1C(Br)=C(CCCCCCCC)C=C1C(C1=NSN=C11)=CC=C1C1=CC(CCCCCCCC)=C(Br)S1 AMYLTENEOQNKGO-UHFFFAOYSA-N 0.000 description 1
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 description 1
101100059612 Caenorhabditis elegans ceh-17 gene Proteins 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
229920005603 alternating copolymer Polymers 0.000 description 1
239000002322 conducting polymer Substances 0.000 description 1
229920001940 conductive polymer Polymers 0.000 description 1
238000009510 drug design Methods 0.000 description 1
239000012776 electronic material Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000005286 illumination Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000002114 nanocomposite Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920002098 polyfluorene Polymers 0.000 description 1
229920000123 polythiophene Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000007639 printing Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000012995 silicone-based technology Methods 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
238000010129 solution processing Methods 0.000 description 1
238000004528 spin coating Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- C08G61/125—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 oxygen 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
- 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
- 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
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
- 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
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B10/00—Integration of renewable energy sources in buildings
- Y02B10/10—Photovoltaic [PV]
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

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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)
Photovoltaic Devices (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

CA002625306A 2008-03-11 2008-03-11 Oligothiophenes regioreguliers a noyau d'accepteurs d'electrons, utilises comme elements constitutifs de polymeres conjugues solubles a faible energie interbande Abandoned CA2625306A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002625306A CA2625306A1 (fr)	2008-03-11	2008-03-11	Oligothiophenes regioreguliers a noyau d'accepteurs d'electrons, utilises comme elements constitutifs de polymeres conjugues solubles a faible energie interbande

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002625306A CA2625306A1 (fr)	2008-03-11	2008-03-11	Oligothiophenes regioreguliers a noyau d'accepteurs d'electrons, utilises comme elements constitutifs de polymeres conjugues solubles a faible energie interbande

Publications (1)

Publication Number	Publication Date
CA2625306A1 true CA2625306A1 (fr)	2009-09-11

Family

ID=41060213

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002625306A Abandoned CA2625306A1 (fr)	2008-03-11	2008-03-11	Oligothiophenes regioreguliers a noyau d'accepteurs d'electrons, utilises comme elements constitutifs de polymeres conjugues solubles a faible energie interbande

Country Status (1)

Country	Link
CA (1)	CA2625306A1 (fr)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2010041687A1 (fr) *	2008-10-09	2010-04-15	コニカミノルタホールディングス株式会社	Élément de conversion photoélectrique organique, cellule solaire, et réseau de capteurs optiques
WO2011060526A1 (fr) *	2009-11-18	2011-05-26	National Research Council Of Canada	Monomères, oligomères et polymères fluorés utilisables dans des dispositifs électroniques organiques
EP2333017A1 (fr)	2009-10-26	2011-06-15	Taiwan Textile Research Institute	Nouveau dopant de colorant, composition le comportant et dispositif photovoltaïque incluant cette composition
CN102153732A (zh) *	2011-01-10	2011-08-17	常州大学	立构规整噻吩齐聚物与苯并噻二唑的共聚物及其制备方法
US20120156829A1 (en) *	2009-08-28	2012-06-21	Zhikuan Chen	Polymeric semiconductors, devices, and related methods
CN102786669A (zh) *	2012-07-30	2012-11-21	常州大学	一种聚合物半导体材料和制备方法及其用途
CN103280531A (zh) *	2013-05-10	2013-09-04	中国科学院长春应用化学研究所	聚合物太阳能电池
US8624232B2 (en)	2009-08-28	2014-01-07	Prashant Sonar	Ambipolar polymeric semiconductor materials and organic electronic devices
WO2014074027A1 (fr) *	2012-11-07	2014-05-15	Lanxess Deutschland Gmbh	Polymères et leur utilisation dans des dispositifs photovoltaïques
US20140142308A1 (en) *	2011-03-08	2014-05-22	Nankai University	Photoelectric materials and preparation thereof
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2008
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2011-03-11	FZDE	Discontinued