CN103080116A - 一类苝四羧酸二酰亚胺有机半导体材料及其制备方法和应用 - Google Patents
一类苝四羧酸二酰亚胺有机半导体材料及其制备方法和应用 Download PDFInfo
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- CN103080116A CN103080116A CN2010800689476A CN201080068947A CN103080116A CN 103080116 A CN103080116 A CN 103080116A CN 2010800689476 A CN2010800689476 A CN 2010800689476A CN 201080068947 A CN201080068947 A CN 201080068947A CN 103080116 A CN103080116 A CN 103080116A
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- semiconducting materials
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- benzene
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- 229910000071 diazene Inorganic materials 0.000 title claims abstract description 38
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 239000000463 material Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 title abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 127
- 229930192474 thiophene Natural products 0.000 claims description 51
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 50
- 239000004065 semiconductor Substances 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 35
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 34
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 24
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- 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 claims description 10
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- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
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- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 claims description 4
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- 238000004062 sedimentation Methods 0.000 description 10
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
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- 238000010521 absorption reaction Methods 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- CRBREIOFEDVXGE-UHFFFAOYSA-N dodecoxybenzene Chemical compound CCCCCCCCCCCCOC1=CC=CC=C1 CRBREIOFEDVXGE-UHFFFAOYSA-N 0.000 description 4
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
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- 230000004888 barrier function Effects 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
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- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
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- RPQOZSKWYNULKS-UHFFFAOYSA-N 1,2-dicarbamoylperylene-3,4-dicarboxylic acid Chemical class C1=C(C(O)=O)C2=C(C(O)=O)C(C(=N)O)=C(C(O)=N)C(C=3C4=C5C=CC=C4C=CC=3)=C2C5=C1 RPQOZSKWYNULKS-UHFFFAOYSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical group CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical class O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- PJRGDKFLFAYRBV-UHFFFAOYSA-N 2-phenylthiophene Chemical class C1=CSC(C=2C=CC=CC=2)=C1 PJRGDKFLFAYRBV-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- VGWBXRXNERKBSJ-UHFFFAOYSA-N dithieno[2,3-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2SC=C1 VGWBXRXNERKBSJ-UHFFFAOYSA-N 0.000 description 1
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- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical group C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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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- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
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- H05B33/00—Electroluminescent light sources
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- 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
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- 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
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- 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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Abstract
公开了由下式(I)所示的苝四羧酸二酰亚胺有机半导体材料,属于光电子材料领域。在式(I)中,n为1-100之间的整数;R1、R2或R3为氢、C1-C20烷基、C1-C20烷氧基、苯基或烷氧基苯基;R4或R5为C1-C20烷基;R6或R7为氢、C1-C20烷基、C1-C20烷氧基或苯基。还公开了所述苝四羧酸二酰亚胺有机半导体材料的制备方法和应用。
Description
PCT国内申请,说明书已公开。
Claims (1)
- PCT国内申请,权利要求书已公开。
Applications Claiming Priority (1)
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PCT/CN2010/076802 WO2012031403A1 (zh) | 2010-09-10 | 2010-09-10 | 一类苝四羧酸二酰亚胺有机半导体材料及其制备方法和应用 |
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CN103080116A true CN103080116A (zh) | 2013-05-01 |
CN103080116B CN103080116B (zh) | 2015-10-21 |
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US (1) | US8598302B2 (zh) |
EP (1) | EP2615097B1 (zh) |
JP (1) | JP5775587B2 (zh) |
CN (1) | CN103080116B (zh) |
WO (1) | WO2012031403A1 (zh) |
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JP5859872B2 (ja) | 2012-02-17 | 2016-02-16 | 富士フイルム株式会社 | 有機光電変換素子組成物、これを含む薄膜、光電池、これに用いられる有機半導体ポリマー、化合物およびポリマーの製造方法 |
EP2680336A1 (en) * | 2012-06-25 | 2014-01-01 | Tata Steel Nederland Technology B.V. | Photoactive material having an imide based conjugated backbone |
CN105378962B (zh) * | 2013-07-19 | 2017-06-27 | 富士胶片株式会社 | 有机膜晶体管、有机半导体膜及有机半导体材料以及它们的应用 |
JP5972229B2 (ja) * | 2013-07-19 | 2016-08-17 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料 |
JP5972230B2 (ja) * | 2013-07-19 | 2016-08-17 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料 |
CN107057065B (zh) * | 2017-02-16 | 2020-01-14 | 中山大学 | 具有低介电常数的聚合物及降低聚合物介电常数的分子结构设计方法 |
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WO2009098250A1 (en) * | 2008-02-05 | 2009-08-13 | Basf Se | Perylene-imide semiconductor polymers |
WO2010012710A1 (en) * | 2008-07-29 | 2010-02-04 | Solvay Sa | Perylene tetracarboximide derivatives for photovoltaic devices |
CN101709109A (zh) * | 2009-12-28 | 2010-05-19 | 大连理工大学 | 一类梯形共轭聚合物及其制备方法 |
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JP2862753B2 (ja) * | 1992-06-29 | 1999-03-03 | 信越化学工業株式会社 | チオフェン−シロ−ル共重合体およびその製造方法 |
JP2750559B2 (ja) * | 1992-09-16 | 1998-05-13 | 信越化学工業株式会社 | 導電性重合体組成物 |
CN101205229B (zh) * | 2006-12-20 | 2010-04-14 | 中国科学院化学研究所 | 二并苝四羧酸二酰亚胺类化合物及其制备方法 |
EP2581399B1 (en) * | 2010-06-09 | 2019-11-27 | Ocean's King Lighting Science&Technology Co., Ltd. | Conjugated polymer based on perylene tetracarboxylic acid diimide and benzodithiophene and its preparation method and application |
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- 2010-09-10 EP EP20100856865 patent/EP2615097B1/en active Active
- 2010-09-10 JP JP2013527437A patent/JP5775587B2/ja active Active
- 2010-09-10 CN CN201080068947.6A patent/CN103080116B/zh active Active
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WO2010012710A1 (en) * | 2008-07-29 | 2010-02-04 | Solvay Sa | Perylene tetracarboximide derivatives for photovoltaic devices |
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EP2615097A4 (en) | 2014-07-30 |
CN103080116B (zh) | 2015-10-21 |
EP2615097A1 (en) | 2013-07-17 |
US8598302B2 (en) | 2013-12-03 |
JP2013544897A (ja) | 2013-12-19 |
JP5775587B2 (ja) | 2015-09-09 |
WO2012031403A1 (zh) | 2012-03-15 |
US20130165616A1 (en) | 2013-06-27 |
EP2615097B1 (en) | 2015-03-04 |
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