JP6103585B2 - チエノチオフェン−ベンゾジチオフェン共重合体の製造方法 - Google Patents
チエノチオフェン−ベンゾジチオフェン共重合体の製造方法 Download PDFInfo
- Publication number
- JP6103585B2 JP6103585B2 JP2013066760A JP2013066760A JP6103585B2 JP 6103585 B2 JP6103585 B2 JP 6103585B2 JP 2013066760 A JP2013066760 A JP 2013066760A JP 2013066760 A JP2013066760 A JP 2013066760A JP 6103585 B2 JP6103585 B2 JP 6103585B2
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- Prior art keywords
- thienothiophene
- copolymer
- benzodithiophene
- solvent
- palladium
- 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.)
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- 229920001577 copolymer Polymers 0.000 title claims description 98
- 238000004519 manufacturing process Methods 0.000 title claims description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 89
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical class S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 claims description 41
- 239000003054 catalyst Substances 0.000 claims description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- 229910052763 palladium Inorganic materials 0.000 claims description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
- 238000006116 polymerization reaction Methods 0.000 claims description 32
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical class C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 claims description 31
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000012046 mixed solvent Substances 0.000 claims description 15
- 239000007810 chemical reaction solvent Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- -1 boronic acid ester Chemical class 0.000 claims description 12
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 11
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 claims description 11
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- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 8
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