JP5665992B2 - ベンゾジチオフェン有機半導体材料、及び、その調合法 - Google Patents
ベンゾジチオフェン有機半導体材料、及び、その調合法 Download PDFInfo
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- JP5665992B2 JP5665992B2 JP2013527438A JP2013527438A JP5665992B2 JP 5665992 B2 JP5665992 B2 JP 5665992B2 JP 2013527438 A JP2013527438 A JP 2013527438A JP 2013527438 A JP2013527438 A JP 2013527438A JP 5665992 B2 JP5665992 B2 JP 5665992B2
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- organic
- semiconductor material
- organic semiconductor
- benzodithiophene
- dithiophene
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- 239000004065 semiconductor Substances 0.000 title claims description 99
- 239000000463 material Substances 0.000 title claims description 75
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 title claims description 66
- 238000002360 preparation method Methods 0.000 title claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 132
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 54
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 48
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 239000003960 organic solvent Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 21
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 15
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- -1 3,8-dibromo-2,3-disubstituted-quinoxaline Chemical class 0.000 claims description 13
- 229910052763 palladium Inorganic materials 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 12
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 claims description 12
- 229950004394 ditiocarb Drugs 0.000 claims description 12
- 239000003446 ligand Substances 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 11
- 230000005669 field effect Effects 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 claims description 7
- 238000006619 Stille reaction Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- VPMJBJSLTPBZLR-UHFFFAOYSA-N 3,6-dibromobenzene-1,2-diamine Chemical compound NC1=C(N)C(Br)=CC=C1Br VPMJBJSLTPBZLR-UHFFFAOYSA-N 0.000 claims description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 150000003252 quinoxalines Chemical class 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- 239000000084 colloidal system Substances 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 claims 1
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- 239000010410 layer Substances 0.000 description 47
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
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- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 239000001301 oxygen Substances 0.000 description 20
- 229910052760 oxygen Inorganic materials 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
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- 238000011160 research Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 4
- AAXJYOMLFMQERL-UHFFFAOYSA-N 5,8-dibromo-2,3-dioctylquinoxaline Chemical compound C1=CC(Br)=C2N=C(CCCCCCCC)C(CCCCCCCC)=NC2=C1Br AAXJYOMLFMQERL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- MNYKBJCWRPPWIC-UHFFFAOYSA-N 2,7-dibromo-4,5-dioctylthieno[3,2-g][1]benzothiole Chemical compound C1=2SC(Br)=CC=2C(CCCCCCCC)=C(CCCCCCCC)C2=C1SC(Br)=C2 MNYKBJCWRPPWIC-UHFFFAOYSA-N 0.000 description 2
- PGFUDSSXJRHTRU-UHFFFAOYSA-N 4,5-dioctylthieno[3,2-g][1]benzothiole Chemical compound C1=2SC=CC=2C(CCCCCCCC)=C(CCCCCCCC)C2=C1SC=C2 PGFUDSSXJRHTRU-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
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- 230000005855 radiation Effects 0.000 description 2
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- 229930192474 thiophene Natural products 0.000 description 2
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- YSDLVQIOIXINJC-UHFFFAOYSA-N octadecane-9,10-dione Chemical compound CCCCCCCCC(=O)C(=O)CCCCCCCC YSDLVQIOIXINJC-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
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- XUIMIQQOPSSXEZ-AKLPVKDBSA-N silicon-31 atom Chemical compound [31Si] XUIMIQQOPSSXEZ-AKLPVKDBSA-N 0.000 description 1
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- CWJAUGSFNRQHAZ-UHFFFAOYSA-N thieno[3,2-g][1]benzothiole Chemical class C1=C2C=CSC2=C2SC=CC2=C1 CWJAUGSFNRQHAZ-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—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 four or more hetero rings
-
- 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
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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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
- H10K85/113—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
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- H10K85/151—Copolymers
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- 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
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- 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
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- C—CHEMISTRY; METALLURGY
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Description
以下の化学構造式(式3)で示される2,7−ジブロモ−ベンゾ−〔2,1−b:3,4−b’〕ジチオフェン
化学構造式が以下の構造式(式4)で表される、5,8−ジ−(5−ブロモ−2−チェニル)−2,3−二置換−キノキサリン
シュティレカップリング反応を24〜72時間実行し、
条件は、モル比m:p:q(m=p+q、m、p、qは正の実数)とし、温度は60℃〜132℃とし、第一の触媒と第一の有機溶媒の環境下とし、これにより、以下の化学構造式(式5)で表されるベンゾジチオフェン有機半導体材料を含む反応混合物が得られる。
3,6−ジブロモ−o−フェニレンジアミンとアルキルエタンジオンが混合され、以下に示される反応式により、5,8−ジ−(5−ブロモ−2−チェニル)−2,3−二置換−キノキサリンが準備される。
無酸素環境において、第二の触媒を含む第二の有機溶媒に、5,8−ジ−ブロモ−2,3−二置換−キノキサリン、3−アルキル−2−チオフェンボレート、及び、無水炭酸ナトリウムを加え、5,8−ジ−(4−アルキル−2−チェニル)−2,3−二置換−キノキサリンを得る。ここで、第二の触媒は、有機パラジウム、又は、有機パラジウムと有機りん配位子の混合物であり、第二の有機溶媒は、テトラヒドロフラン、ジエチルエーテル、ジクロロメタン、クロロホルム、および酢酸エチルを含むグループから少なくとも一つが選択され、その反応式は以下の通りである。
第一の有機溶媒は、少なくともテトラヒドロフラン(THF:以下同じ)、ジメトキシエタン、ベンゼン、クロロベンゼン、又は、トルエンから選択されたものの1つである。
実施例1
本実施例1のベンゾジチオフェン有機半導体材料は、以下の化学構造式を有する:
本実施例2のベンゾジチオフェン有機半導体材料は、以下の化学構造式を有する:
実施例3
図1にポリマー太陽電池デバイスの構造を示す。本実施例では、基板はITOガラスであり、ガラスは基板として使用され、ITOが導電層として使用される。
約50〜300nmの厚み有する陽極となる導電層を形成するために、10〜20Ω/sqのシート抵抗を有する酸化インジウムスズ(ITO)12の一層を、ガラス基盤11の1側の表面に蒸着させる。
図2に有機エレクトロルミネッセンスデバイスの構造を示す。本実施例では、基板はITOガラスであり、ガラスは基板として使用され、ITOが導電層として使用される。
約50〜300nmの厚み有する陽極となる導電層を形成するために、10〜20Ω/sqのシート抵抗を有する酸化インジウムスズ(ITO)22の一層を、ガラス基盤21の一側の表面に蒸着させる。ITOは、好ましくは、10Ω/sqのシート抵抗を有する。
実施例5
図3に有機電界効果トランジスタの構造を示す。本実施例では、基板はドープされたシリコン(Si)である。
Claims (10)
- ベンゾジチオフェン有機半導体材料の調合法であって、以下のステップを含む。
無酸素環境で、
化学構造式(式38)で示される2,7ビス(トリメチルすず)−ベンゾ−〔2,1−b:3,4−b’〕ジチオフェン
化学構造式(式39)で示される2,7−ジブロモ−ベンゾ−〔2,1−b:3,4−b’〕ジチオフェン
化学構造式(40)で示される5,8−ジ−(5−ブロモ−2−チェニル)−2,3−二置換−キノキサリン
第一の触媒と第一の有機溶媒の環境下で、シュティレカップリング反応を実施して化学構造式(式41)で示されるベンゾジチオフェン有機半導体材料
ここで、x+y=2、1≦x<2,0<y≦1、1<n≦100、R1,R2は、C1〜C20アルキル基であり、R3は、C1〜C20アルキル基から選択され、R4,R5は、C1〜C20アルコキシ基によって置換された水素、フェニル基、C1〜C20アルキル基またはフェニル基である。 - 前記5,8−ジ−(5−ブロモ−2−チェニル)−2,3−二置換−キノキサリンが、
3,6−ジブロモ−o−フェニレンジアミンとエトキシル化ジオンを混合、反応させ、5,8−ジブロモ−2,3−二置換−キノキサリンを準備する第一ステップと、
無酸素環境において、第二の触媒を含む第二の有機溶媒に、5,8−ジブロモ−2,3−二置換−キノキサリン、3−アルキル−2−チオフェンボレート、及び、無水炭酸ナトリウムを加え、5,8−ジ−(4−アルキル−2−チェニル)−2,3−二置換−キノキサリンを反応によって得る第二ステップであって、
前記第二の触媒は、有機パラジウム、又は、有機パラジウムと有機りん配位子の混合物であり、
前記第二の有機溶媒は、テトラヒドロフラン、ジエチルエーテル、ジクロロメタン、クロロホルム、および酢酸エチルを含むグループから少なくとも一つが選択される、
第二ステップと、
無酸素環境において、N−ブロモスクシンイミドと5,8−ジ−(4−アルキル−2−チェニル)−2,3−二置換キノキサリンが、硫酸とトリフルオル酢酸の混合溶媒に加えられ、10℃〜30℃において12〜48時間反応され、5,8−ジ−(4−アルキル−2−チェニル)−2,3−二置換−キノキサリンを得る第三ステップと、
により、準備される、ことを特徴とする請求項2に記載のベンゾジチオフェン有機半導体材料の調合法。 - 前記2,7ビス(トリメチルすず)−ベンゾ−〔2,1−b:3,4−b’〕ジチオフェンが、
−78℃から−25℃の間の温度で、4,5−ジアルキルベンゾ〔2,1−b:3,4−b’〕ジチオフェンとブチル基リチウムが第三の有機溶媒に滴下して加えられ、そこに、トリメチルすずクロリドが、2,7ビス(トリメチルすず)−ベンゾ−〔2,1−b:3,4−b’〕ジチオフェンを準備するために加えられる第四ステップであって、
前記第三の有機溶媒は、テトラヒドロフラン、ジエチルエーテル、ジクロロメタン、クロロホルム、および酢酸エチルを含むグループから少なくとも一つが選択される第四ステップ、
により、準備される、ことを特徴とする請求項2に記載のベンゾジチオフェン有機半導体材料の調合法。 - 2,7−ジブロモ−ベンゾ−〔2,1−b:3,4−b’〕ジチオフェンが、以下のステップで準備される請求項2に記載のベンゾジチオフェン有機半導体材料の調合法:
無酸素環境において、N−ブロモスクシンイミドと、4,5−ジアルキルベンゾ〔2,1−b:3,4−b〕ジチオフェンが硫酸とトリフルオル酢酸の混合溶媒に加えられ、10℃〜30℃において12〜48時間反応され、4,4−ジアルキル−2,6−ジブロモ−シクロペンタ〔2,1−b:3,4−b’〕ジチオフェンを得るステップ。 - 前記第一の触媒の添加量は,全物質の合計のモル量の0.01%〜30%であり、ここで、第一の触媒は、有機パラジウム、又は、有機パラジウムと有機りん配位子の混合物であり、
有機パラジウムは、Pd2(dba)3,Pd(PPh3)4またはPd(PPh3)2Cl2の少なくとも一つから選択され、
有機ホスフィン配位子は、P(o−Tol)3であり、
有機パラジウムと有機ホスフィン配位子の混合物において、有機パラジウム対有機ホスフィン配位子のモル比は、1:1〜1:20とする、
請求項2に記載のベンゾジチオフェン有機半導体材料の調合法。 - 前記第一の有機溶媒は、少なくともテトラヒドロフラン、エチレングリコールジメチル、ベンゼン、クロロベンゼン、又は、トルエンから選択されたものの1つである、
請求項2に記載のベンゾジチオフェン有機半導体材料の調合法。 - 前記シュティレカップリング反応において、2,7ビス(トリメチルすず)−ベンゾ−〔2,1−b:3,4−b〕ジチオフェンと、2,7−ジブロモ−ベンゾ−〔2,1−b:3,4−b’〕ジチオフェンと、5,8−ジ−(5−ブロモ−2−チェニル)−2,3−二置換−キノキサリンのモル比率がm:p:qであり、m=p+qであり、m、p、qが正の実数であり、シュティレカップリング反応の反応温度は60℃〜132℃であり、反応時間は24〜72時間である、
請求項2に記載のベンゾジチオフェン有機半導体材料の調合法。 - 請求項2に記載のベンゾジチオフェン有機半導体材料の調合法であって、シュティレカップリング反応の後に、さらに反応混合物を精製する以下のステップを含む:
反応混合物を、メタノールに滴状で加え、沈降処理の後、吸引フィルタリングを実施し、メタノールで洗浄し、乾燥させ、有機半導体材料を含むコロイド得るステップ;
有機半導体材料を含むトルエン溶液を得るために、コロイドをトルエンに溶解させるステップ;
有機半導体材料を含むトルエン溶液をナトリウムジエチルジチオカルバメート水溶液に加え、80℃−100℃で加熱、攪拌をし、有機半導体材料を分離するためにアルミナクロマトグラフィーカラムに混合物溶液を通して、クロロベンゼンを含んで溶出させた後、クロロベンゼン系有機溶媒の減圧除去がなされ、最終的に、アセトンソックスレーで有機半導体材料を抽出し、固形の有機半導体材料を得るステップ。 - ポリマー太陽電池、有機エレクトロルミネセンスデバイス、有機電界効果トランジスタ、有機光学ストレージ、有機非線状デバイス、又は、有機レーザーデバイスに用いられる、請求項1に記載のベンゾジチオフェン有機半導体材料。
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KR101314931B1 (ko) * | 2006-10-30 | 2013-10-04 | 삼성전자주식회사 | 유기 고분자 반도체, 이의 제조방법 및 이를 이용한 양극성 유기 박막 트랜지스터 |
US8530889B2 (en) * | 2008-05-12 | 2013-09-10 | Toray Industries, Inc. | Carbon nanotube composite, organic semiconductor composite, and field-effect transistor |
JP5655267B2 (ja) * | 2008-11-10 | 2015-01-21 | 東レ株式会社 | キノキサリン化合物、これを用いた電子供与性有機材料、光起電力素子用材料および光起電力素子 |
CN101407574B (zh) * | 2008-12-01 | 2011-11-23 | 中国科学院长春应用化学研究所 | 含二噻吩并吡咯的给体-受体型共轭聚合物及制法和应用 |
JP5533646B2 (ja) * | 2009-01-20 | 2014-06-25 | 東レ株式会社 | 光起電力素子用材料および光起電力素子 |
JP2013523931A (ja) * | 2010-03-31 | 2013-06-17 | ビーエーエスエフ ソシエタス・ヨーロピア | 縮合環系ジチオフェンコポリマー |
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