TWI374881B - Pentathienyl-fluorene copolymer - Google Patents
Pentathienyl-fluorene copolymer Download PDFInfo
- Publication number
- TWI374881B TWI374881B TW094107129A TW94107129A TWI374881B TW I374881 B TWI374881 B TW I374881B TW 094107129 A TW094107129 A TW 094107129A TW 94107129 A TW94107129 A TW 94107129A TW I374881 B TWI374881 B TW I374881B
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- Taiwan
- Prior art keywords
- group
- copolymer
- patent application
- hexyl
- linear
- Prior art date
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- 229920001577 copolymer Polymers 0.000 title claims description 27
- -1 n-octyl Chemical group 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000004065 semiconductor Substances 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 229910052710 silicon Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 19
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 8
- 229910052737 gold Inorganic materials 0.000 description 8
- 239000010931 gold Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- KXSFECAJUBPPFE-UHFFFAOYSA-N 2,2':5',2''-terthiophene Chemical class C1=CSC(C=2SC(=CC=2)C=2SC=CC=2)=C1 KXSFECAJUBPPFE-UHFFFAOYSA-N 0.000 description 1
- ATRJNSFQBYKFSM-UHFFFAOYSA-N 2,3-dibromothiophene Chemical compound BrC=1C=CSC=1Br ATRJNSFQBYKFSM-UHFFFAOYSA-N 0.000 description 1
- YJMJDAXLNHAHAQ-UHFFFAOYSA-N 2,5-dibromo-3,4-dihexylthiophene Chemical compound CCCCCCC1=C(Br)SC(Br)=C1CCCCCC YJMJDAXLNHAHAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- VZJVVQFCOUNGRH-UHFFFAOYSA-M C[Sn](C)(C)Cl.[Sn] Chemical compound C[Sn](C)(C)Cl.[Sn] VZJVVQFCOUNGRH-UHFFFAOYSA-M 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- BYDQGSVXQDOSJJ-UHFFFAOYSA-N [Ge].[Au] Chemical compound [Ge].[Au] BYDQGSVXQDOSJJ-UHFFFAOYSA-N 0.000 description 1
- PDURERVQKAJCAK-UHFFFAOYSA-N [Zn]C1=CC=CS1 Chemical class [Zn]C1=CC=CS1 PDURERVQKAJCAK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 description 1
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical class N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-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
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link 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
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- 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
-
- 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
-
- 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
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- 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
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- 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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- 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
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- 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
- H10K85/115—Polyfluorene; Derivatives thereof
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Physics & Mathematics (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Thin Film Transistor (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Description
1374881 第94107129號專利申請案說明書替換本修正日期:101年1月5曰 九、發明說明: 【發明所屬之技術領域3 相關文獻聲明 t 本申請案主張2004年3月17曰申請的美國臨時申請案 5 第60/554,218號之利益。 政府契約 本發明係基於美國政府支持由NIST所授予之第 70NANB0H3033號合作協議而完成。美國政府對本發明具 •有一定程度的權利。 10 發明背景 本發明係關於五噻吩基-苐共聚物。 I:先前技術3 為了最佳化運作,電晶體必需在狹窄的電壓範圍内被 開啟及關閉。用來致動一電晶體所需的電壓稱作底限電 15 壓,其穩定度係視電晶體内的半導體材料特性而定。許多 被運用在電晶體應用的半導體材料並不適當,這是因為使 • 用該等材料會導致底限電壓高變異性的緣故。因此,就半 導體用於電晶體應用之領域而言,尋找具有低底限電壓變 ' 異性的半導體係一不間斷的挑戰。 20 【發明内容】 發明概要 本發明係藉由提供一第一態樣來滿足本領域之一課 題,該第一態樣係一具有以下式表示的結構單位之五噻吩 基-第共聚物: 5 1374881 第94107129號專利申請案說明書替換本修正日期:101年1月5曰
其中R與R’係各分別為一取代基或Η。 在第二態樣中,本發明係一包含半導體電晶體通道的 電晶體,該通道係由一具有以下式表示的結構單位之五噻 5 吩基-薙共聚物所構成:
其中R與R’係各分別為一取代基或Η。本發明係藉由提供一 具有極低的磁滞(hysteresis)之電致動元件來滿足本領域的 一課題。 10 圖式簡單說明 第1圖係一包覆有五噻吩基-第共聚物之電晶體的構 形。
【實施方式:J 發明詳細說明 15 本發明第一態樣係關於一具有以下式表示的結構單位 之五噻吩基-苐共聚物: 第94107129號專利申請案說明書替換本修正日期:1〇1 年1月5日
其令R與R,係各分別為-取代基或H。該共聚物係較佳為經 取代者,以便能適當地溶於有機㈣,俾使所得溶液可塗 覆至一基板以形成電晶體。 巴含Ci-Cm直鏈或支鏈烷基基 團、C5-C3。芳基基團或C6-C4。芳院基基團,或兩她基團一 起和第基基_9··、子形成C52。職結構 任擇地包含—或多個雜原子,例如〇、s、N、PstSi^ 地,各個R係分別為C5-C12直鍵 烧基或以成基鮮基。最隹2°炫氧基 双佳地,各個尺係正己基、正辛 基或正己基經苯基。較佳地,各槪,係分別為Ci_C^ 支鏈烧基或是C丨-C3〇烷氧基烷基 Η” Γ Γ… 各做,係分別為 Η或疋Cl_Cl2直鏈或支舰基。.五料基基團的 未經取代的五嘍吩基基團、3' 4”-二取代_α-五射基基團,如下所示五料基基團或3”,
其中R’先前已有定義。 二溴五噻吩和2,7·苐二 製備。較佳地,2,7-苐 本發明之共聚物可藉由聘5,5,,,,_ 棚酸醋偶合或和2,7-苐二爛峻偶人來 1374881 5 第94107129號專利申請案說明書替換本修正日期:101年1月5曰 二硼酸酯或二硼酸係9,9-二取代-2,7-苐二硼酸酯或二硼 酸;該5,5'…-二溴五噻吩係較佳為5,5'"'-二溴-3",4’’-二烷基 -α-五噻吩。9,9-二取代-2,7-苐二硼酸酯可由任何適宜方法 製備,例如此領域所熟知的那些方法,舉例來說,如揭示 於美國專利第6,169,163號第37欄65-67行及第38欄1-40行的 方法,該說明内容係併入本文以供參照。一較佳的二溴五 噻吩可根據下列反應流程來製備:
又,各種多取代二溴化五噻吩可藉由一開始將一經取 10 代或未經取代的三噻吩和一經取代或未經取代的噻吩偶合 1374881 第94107129號專利申請案說明書替換本修正日期:101年1月5曰 來製備,如下所例示:
必須要瞭解到的是2-噻吩基三烷基錫與2-二噻吩基三 烷基錫並不是可以和2,5-二溴化噻吩偶合的試劑的唯一例 5 子。其他例子包括鹵化(2-噻吩基)鋅和鹵化(2-二噻吩基) 鋅,較佳為2-氣化(2-噻吩基)辞和2-氣化(2-二噻吩基)鋅, 其可由修改過的根岸(Negishi)交聯偶合反應製備(參見E. Negishi 等人,J. Org. Chem. 42, 1821 (1977));而2-噻吩硼 酸與2-二噻吩硼酸或該等之硼酸酯則可使用修改版的鈐木 10 (Suzuki)交聯偶合反應來製備(參見Miyaura等人發表於 Chemical Revews,Vol. 95, pp. 2457-2483 (1995))。 1374881 第94107129號專利申請案說明書替換本修正日期:1〇1年丨月5日 製備各種經取代嘍吩偶合劑的多個例子包括有a)在氯 化鎳催化劑的存在下使3,4-二溴噻吩與烷基化葛林納試劑 (例如溴化(烷基)鎂)反應以形成3,4·二烷基噻吩,然後使該 中間產物和氯化(三甲基)錫反應以形成3 4_二烷基_2_嘍吩 5基二烷基錫;b)使2_溴烷基噻吩與鎂反應以生成葛林納 試劑,然後使該中間產物和齒化鋅反應以形成齒化(3_烷基 •2-嘍吩基)鋅;或c)在胺(例如N,N,n,,n,-四甲基乙二胺 (TMEDA)或三異丙胺)的存在下使3_烷基噻吩與正丁基鋰 反應以形成4-烷基-2-噻吩基鋰中間產物,然後使該中間產 10物和鹵化鋅反應以形成函化(4-烷基-2-噻吩基)鋅。 本發明之共聚物亦可包括另外的伸芳基結構單位,包 括經取代或未經取代的伸噻吩基、二伸噻吩基、1,4_伸苯 基、4,4,-二伸苯基、蔥_9,1〇_二基、萘·M_二基、萘-2,6_二 基、2,1,3-苯幷噻二唑·4,7-二基、N-取代-咔唑-3,8-二基、 15 N•取代·咔唑-4,7-二基、二苯幷矽唑_3,8_二基、二苯幷矽唑 一4,7-二基、N-取代-争g讲-3,7-二基、N-取代噚畊-3,7-二 基、三芳基胺二基(包括三苯基胺-4,4,-二基、二苯基對甲苯 基胺-4,4,·二基與n,N-二苯基苯胺-3,5-二基)、N,N,N,,N,-四芳 基-1,、二胺基笨-二基、n,N,N,,N,-四芳基聯苯胺-二基、芳基矽 20烷-二基。 在第二態樣中,本發明係一包含半導體電晶體通道的 電晶體,該通道係由五噻吩基-苐共聚物所構成。一較佳的 底部閘極型共面電晶體之圖式係繪於第!圖。電晶體(1〇)包 含一共聚物層(20),該共聚物層係疊置於金製源極接觸部 10 第94107129號專利申請案說明書替換本修正日期如年^月5曰 (3〇)、金製汲極接觸部⑽)及氮化残極介電質⑽上。該 源極接_(30)歧極接觸部(4G)通常具有比介電質⑽高 約20 - UK) nm的高度。介電質(5〇)(其具有通常介於〇」_ 觸毫微法㈣之電容)·以及任擇的共聚物係4置於金製 閘極(60)與基板(7G)上,該基板可為玻璃或—例如塑膠之可 撓材料。通道長度(源極接觸部(30)與汲極接觸部(4〇)之間的 距離)通常係介於1 —議微米。通道寬度⑺)通常落於顺 米至10 mm之範圍内。可以一溶液(譬如於二甲苯中〇5 _ 4 重量百分比)將共聚物層(2〇)(通常厚1〇 _ 20〇 nm)用各種技 術塗覆至該元件’包括旋轉塗佈法、喷墨塗佈法或浸潰塗 佈法。該金製源極接觸部(30)、金製汲極接觸部(40)及金製 閘極(60)可一舉例來說—以濺鍍法或蒸發法來塗覆。氮化矽 閘極介電質(5 0)可一舉例來說一以化學氣相沈積法來塗覆。 已驚人地發現到本發明的共聚物可被用來製造具有極 低底限電壓變異性的電晶體。 下列實施例僅用於例示目的而非意欲限制本發明之範 實施例1 -5, 5””-二溴·3”,4”-二己基-α-五噻吩的合成
Α_ 5-三甲錫基_2,2’-二噻吩的製備 1374881 第94107129號專利申請案說明書替換本修正曰期:101年1月5曰 ^3~SnMe3 將2,2’-二噻吩(1〇 g,60.1 mmol)及無水THF(lOOmL)加 進一配備有玻璃塞、橡膠隔片和氮氣進氣口的三頸燒瓶 裡。使該暗色(綠色)溶液冷卻至0°c。將n-BuLi溶於己烷之 5 2·5 Μ溶液(26_4 mL,66 mmol)以注射加入。然後使反應混合 物在25°C下攪拌1.5小時。使該混合物冷卻至-78°C並經由注 射將氣化(二甲基)錫溶於THF之1 ·〇 Μ溶液(66 mL, 66mmol) 緩緩加入。使反應混合物回溫至25°C並授拌過夜。抽真空 將THF移除並將殘餘物溶於戊烷(2〇〇 mL)。將該戊烷層以水 10 (3 x 200 mL)沖洗、用MgS04乾燥並抽真空將戊烷移除以生 成一綠色油狀物。以真空蒸餾(118-120。(:,0.6 mmHg)純化 該油狀物以生成12_5g (64%)產物。MS = 330 » B. 2,5-二溴-3, 4-二己基噻吩的製備
將溶於DMF(80 mL)的3,4,-二己基嘆吩(2〇.i4g,0.0797 mol)加進一配備有玻璃塞、橡膠隔片以及一連接至氮氣進 氣口之迴流冷凝器的250mL三頸圓底燒舰裡。將nbs(28.37 g,0.159 mol)加至該溶液並使混合物在室溫下搜拌15小 時。然後將反應混合物倒入水中並以戊烷(3 X 200 mL)萃 2〇取。將合併的戊烧分層用水(3 X 300 mL)沖洗、用MgS〇4乾 12 1374881 第94107129號專利申請案說明書替換本修正日期:〗〇1年丨月5曰 餘,在那之後抽真空將戊烧移除以生成一澄清的黃色油狀 物。以真空蒸餾(135。(:,0.6 mmHg)純化該油狀物以生成28 〇 g (77%)的淡黃色油狀物。MS = 410。 , C_ 3”,4”-二己基-α-五噻吩的製備 5 將5-三曱錫基-2, 2,-二噻吩(8_28g, 25 mmol)、2,5-二漠 -3, 4-二己基嘆吩(4.92 g,25 mmol)及DMF(100 mL)加進一 配備有玻璃塞、橡膠隔片以及一連接至氮氣進氣口之迴流 冷凝器的250mL三頸圓底燒瓶裡β使燒瓶通氮氣1〇 min,然 • 後加入Pd(PPh3)2Cl2 (0.35 g,25 mmol)溶液並使暗色混合物 10 於90°C加熱18 h。使該溶液冷卻、將其倒入一 3% NaCl溶於 水中之溶液(800 mL) ’用謎(3 X 200 ml)萃取該水性混合 物。將合併的醚層用3% NaCl溶於水中之溶液(3 X 200 mL) 沖洗、用MgS〇4乾燥並抽真空將醚移除以生成一橙色固 體。將乙醇(500 mL)加至該粗產物且加熱至9〇°c直到固體 15 溶解。將乙醇傾析至一乾淨燒瓶並以過濾法收集沈澱物。 產率:5.70 g,81%。 # D· 5, 5’’’’-二溴。”,斗”-二己基-…五噻吩的合成 將3”,4,’·二己基-α-五嘍吩(7.02 g,12_8 mmol)、THF ' (150mL)與乙酸(75 mL)加進一配備有玻璃塞、附加漏斗以 20 及一連接至氮氣進氣口之迴流冷凝器的250mL三頸圓底燒 瓶裡。在該附加漏斗中’ NBS(4.19 g, 23.56 mmol)係溶於 THF(50 mL)與乙酸(25 mL)。於〇°C將該溶液以超過45分鐘 逐滴加入該3”,4”-二己基-α-五嘴吩溶液。使反應混合物再 攪拌45分鐘,然後用LC監測。將另外的NBS(0.32 g,1.83 13 1374881 第94107129號專利申請案說明書替換本修正日期:1〇丨年丨月5日 mmol)加入該反應混合物’再繼續擾掉15分鐘。將蒸鶴水 (500 mL)加至反應混合物並以過濾法收集沈殿固體。該固 體係以10% NaHC〇3與水沖洗,然後用硫酸鎂乾燥。將該固 體再溶解於CH2Cl2(200ml),然後通過矽膠,再接著用CH2Cl2 5 (200 mL)沖洗。隨後抽真空使溶劑蒸發以生成一橘色固 體。該橘色固體係以丙嗣結晶。產率_· 8.1 g,90 %。 實施例2-五噻吩基-荞共聚物的製備 將9,9-二辛基苐-2,7-二硼酸酯(3.77 g,7.10 mm〇l)、5, 5’’’’-二溴-3”,4”-二己基-α-五噻吩(5·65 g,7.66mmol)、 10 Aliquot 336相轉移催化劑(0.87g,02.16mmol)、[Pd(PPh3)2Cld (0.0073 g,0.010 mm〇l)以及甲笨(92 mL)加進一安裝有迴流 冷凝器(伴有氮氣進氣口與塔頂攪拌子)的25〇mL三頸圓底 燒瓶裡。在攪拌數分鐘以溶掉大部分固體之後,加入碳酸 納溶液(2 M,13.1 mL, 26.2 mmol)。然後將反應混合物於95 15 °C加熱5小時。然後加入溶於THF(l〇 ml)之苯基硼酸(0.46 g,
3_77 mmol)及[Pd(PPh3)2Cl2] (0.0073g,0.010 mmol),於95°C 下繼續攪拌16小時。將反應混合物以甲笨(230 mL)稀釋, 有機層被分離並以溫水(3 x 230 mL)沖洗。該溶液隨後以二 己基二硫代胺基甲酸鈉鹽三水合物(7.5 %, DDC,76.6 mL) 20的水溶液處理並於8〇t加熱過夜。將水層分離並丟棄,而 有機層則以溫水(3 X 230 mL)沖洗,聚合物係沈澱於曱醇 (2_3 L)中。該聚合物係以過濾法收集、以甲醇(2〇〇 mL)沖 洗、然後再溶解於熱曱苯(960 mL)中,其中60 mL的熱甲苯 將被煮掉。將該熱聚合物溶液通過緊密填塞有次乙醯塑料 14 第94107129號專利申請案說明書替換本修正日期:ιοί年i月5曰 (celite ’ 1 X 8 cm)、石夕膠(4 X 8 cm)及驗性氧化銘(3 X 8 cm) 的管柱(先以200 mL熱甲苯沖過)。收集該聚合物溶液,隨 後將該溶液的體積濃縮至大約500 mL。將聚合物沈澱於曱 醇(2·3 L)’以甲醇(230 mL)、丙明(230 mL)及再次以甲醇 (230 mL)沖洗該聚合物。然後於6〇°C抽真空過夜將聚合物 乾燥以生成橘红色材料。產率:5.59g。 實施例3-製備及測試包含五嘍吩基·第共聚物的電晶體 使用〇2電漿去光阻機清潔預先製備之多層結構的表面 以去除有機殘餘物’該多層結構係實質上如同第1圖所繪之 元件(30) - (70)。隨後以去離子水潤洗該等表面,然後乾 燥。各結構係具有1 mm之通道寬度,各包含一玻璃基板、 金製閘極、閘極介電質(電容〜22 nF)、金製源極(高度〜70 nm) 及金製淡極(高度〜70 nm)。該等結構之通道長度係自5 /zm 至50 不等。實質上如第1圖所繪之電晶體元件係藉由旋 轉塗佈一如實施例2般製備之五噻吩基-苐共聚物的1%二甲 苯溶液來製備。表1展示第一電壓掃描之估計底限電壓 (VT。)、電荷攜帶移動度(pfe)以及多次連續掃描之間的底限 電壓差異(△%,亦習知為磁滯)。Δντι係指一天後的磁滞且 VT7係指七天後的磁滯現象。 1374881 第94107129號專利申請案說明書替換本修正日期:101年1月5日 表1 -電晶體特性之量測 閘極長度 50 μπι 閘極長度 20 μπι 閘極長度 10 μπι 閘極長度 5 μιη (cm2/V-sec) 4.62 xlO-4 8.73 xlO'4 1.01 Χίο.3 2_27 xlO·3 ντ° 2 V 2 V 3 V 8 V △VT1 ον ον ον ον △Vt7 ον ον ον ον 【圖式簡單說明】 第1圖係一包覆有五°塞吩基-苐共聚物之電晶體的構 形。 5 【主要元件符號說明】 10…電晶體 20···共聚物層 30…源極接觸部 40…汲極接觸部 50…介電質 60…閘極 70…基板 16
Claims (1)
1374881 第94107129號專利申請案申請專利範圍替換本修正曰期10$穿1用5曰日I 十、申請專利範圍: |修正本j 1. 一種五噻吩基-第共聚物,其具有以下式表示之結構單 位:
其中,各個R係分別為Η、CrC2G直鏈或支鏈烷基、 C5-C30芳基或C6-C40芳烷基,或兩個R基團一起和苐基基 團的9-碳原子形成C5_2〇環狀結構; 各個R基團可任擇地包含一或多個雜原子0、S、N、 P或Si ;及 各個R’係分別為Η、CVCm直鏈或支鏈烷基或CVCm 烧氧基烧基。 2.如申請專利範圍第1項之五噻吩基-苐共聚物,其中各個 ® R係正己基、正辛基或正己基羥苯基且各個R’係分別為 Η或是CrCu直鏈或支鏈烷基。 ' 3.如申請專利範圍第1項之五噻吩基-苐共聚物,其包含以 下式表示之五噻吩基結構單位:
17 1374881 第94107129號專利申請案申請專利範圍替換本修正日期:101年1月5曰 4. 如申請專利範圍第3項之五噻吩基-第共聚物,其中至少 一個R’SCVCu直鏈或支鏈烷基。 5. 如申請專利範圍第3項之五噻吩基-第共聚物,其中R’係 正己基或正辛基。 6. —種包含半導體電晶體通道的電晶體,該通道係由一具 有以下式表示的結構單位之五噻吩基-苐共聚物所構 成·
其中,各個R係分別為Η、C, -C2Q直鏈或支鏈烷基、C5-C30 芳基或C6-C4〇芳烷基,或兩個R基團一起和第基基團的 9-碳原子形成C5_2G環狀結構; 各個R基團可任擇地包含一或多個雜原子0、S、N、 P或Si ;及 各個R’係分別為Η、CrCM直鏈或支鏈烷基或CrCso 烧氧基烧基。 7. 如申請專利範圍第6項之電晶體,其中各個R係正己基、 正辛基或正己基羥苯基且各個R’係分別為Η或是CrC12 直鏈或支鏈烷基。 8. 如申請專利範圍第7項之電晶體,其中該五噻吩基-g共 聚物係包含以下式表示之五噻吩基結構單位: 18 1374881 第94107129號專利申請案申請專利範圍替換本修正日期:101年1月5曰
其中各個R’係分別為Η或是q-Cu直鏈或支鏈烷基。 9_如申請專利範圍第8項之電晶體,其中R’係正己基或正 辛基。
19 1374881 第94107129號專利申請案說明書替換本修正曰期:101年1月5曰 七、指定代表圖: (一) 本案指定代表圖為:第(1 )圖。 (二) 本代表圖之元件符號簡單說明: 10…電晶體 20…共聚物層 30…源極接觸部 40…汲極接觸部 50…介電質 60…閘極 70…基板 八、本案若有化學式時,請揭示最能顯示發明特徵的化學式:
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JP (1) | JP4937901B2 (zh) |
KR (1) | KR101169820B1 (zh) |
CN (1) | CN1968986B (zh) |
DE (1) | DE112005000604T5 (zh) |
GB (1) | GB2427866B (zh) |
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FR2869318B1 (fr) * | 2004-04-21 | 2006-06-09 | Commissariat Energie Atomique | Composes mono-,oligo et polymeres pi -conjugues, et cellules photovoltaiques les contenant |
US7781673B2 (en) * | 2005-07-14 | 2010-08-24 | Konarka Technologies, Inc. | Polymers with low band gaps and high charge mobility |
US20070181179A1 (en) | 2005-12-21 | 2007-08-09 | Konarka Technologies, Inc. | Tandem photovoltaic cells |
US7495251B2 (en) * | 2006-04-21 | 2009-02-24 | 3M Innovative Properties Company | Electronic devices containing acene-thiophene copolymers with silylethynyl groups |
US7666968B2 (en) | 2006-04-21 | 2010-02-23 | 3M Innovative Properties Company | Acene-thiophene copolymers with silethynly groups |
JP2008106239A (ja) * | 2006-09-26 | 2008-05-08 | Sumitomo Chemical Co Ltd | 有機光電変換素子及びその製造に有用な重合体 |
US20100084000A1 (en) * | 2006-09-26 | 2010-04-08 | Sumitomo Chemical Company, Limited | Organic photoelectric conversion device and polymer useful for producing the same |
JP5476660B2 (ja) * | 2006-09-26 | 2014-04-23 | 住友化学株式会社 | 有機光電変換素子及びその製造に有用な重合体 |
US8008424B2 (en) | 2006-10-11 | 2011-08-30 | Konarka Technologies, Inc. | Photovoltaic cell with thiazole-containing polymer |
US8008421B2 (en) | 2006-10-11 | 2011-08-30 | Konarka Technologies, Inc. | Photovoltaic cell with silole-containing polymer |
JP5180498B2 (ja) * | 2007-03-20 | 2013-04-10 | 三洋電機株式会社 | 有機半導体材料及びそれを用いた有機トランジスタ |
JP2009026921A (ja) * | 2007-07-19 | 2009-02-05 | Sumitomo Chemical Co Ltd | 有機光電変換素子 |
JP5462998B2 (ja) * | 2007-08-10 | 2014-04-02 | 住友化学株式会社 | 組成物及び有機光電変換素子 |
CN102336893B (zh) * | 2010-07-20 | 2013-10-02 | 海洋王照明科技股份有限公司 | 含噻吩并噻吩和噻吩吡咯二酮单元的芴类共聚物、其制备方法和应用 |
CN103827164B (zh) | 2011-09-29 | 2016-05-25 | 住友化学株式会社 | 高分子化合物及有机光电转换元件 |
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FR2527618A1 (fr) * | 1982-05-25 | 1983-12-02 | Thomson Csf | Polymeres contenant des heterocycles et des noyaux aromatiques et materiaux organiques conducteurs formes a partir de ces polymeres |
JP3865406B2 (ja) * | 1995-07-28 | 2007-01-10 | 住友化学株式会社 | 2,7−アリール−9−置換フルオレン及び9−置換フルオレンオリゴマー及びポリマー |
US5777070A (en) * | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
KR100414394B1 (ko) * | 2001-08-16 | 2004-01-07 | 일진다이아몬드(주) | 신규한 플루오렌계 발광 고분자 및 이를 이용한 전기발광소자 |
US6872801B2 (en) * | 2002-01-11 | 2005-03-29 | Xerox Corporation | Polythiophenes and devices thereof |
US7141644B2 (en) * | 2002-01-11 | 2006-11-28 | Xerox Corporation | Polthiophenes and devices thereof |
US6777529B2 (en) * | 2002-01-11 | 2004-08-17 | Xerox Corporation | Polythiophenes and devices thereof |
EP1475401B1 (en) * | 2003-03-07 | 2009-05-27 | MERCK PATENT GmbH | Mono-, oligo- and polymers comprising fluorene and aryl groups |
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GB2427866A (en) | 2007-01-10 |
TW200533661A (en) | 2005-10-16 |
CN1968986B (zh) | 2010-05-05 |
GB0620329D0 (en) | 2006-11-29 |
KR101169820B1 (ko) | 2012-07-30 |
GB2427866B (en) | 2008-01-30 |
KR20070012367A (ko) | 2007-01-25 |
WO2005092947A1 (en) | 2005-10-06 |
JP2007529596A (ja) | 2007-10-25 |
CN1968986A (zh) | 2007-05-23 |
US20070210302A1 (en) | 2007-09-13 |
DE112005000604T5 (de) | 2007-02-01 |
US7803885B2 (en) | 2010-09-28 |
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