JP6101264B2 - 共役ポリマー - Google Patents
共役ポリマー Download PDFInfo
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- JP6101264B2 JP6101264B2 JP2014520546A JP2014520546A JP6101264B2 JP 6101264 B2 JP6101264 B2 JP 6101264B2 JP 2014520546 A JP2014520546 A JP 2014520546A JP 2014520546 A JP2014520546 A JP 2014520546A JP 6101264 B2 JP6101264 B2 JP 6101264B2
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- 229920000547 conjugated polymer Polymers 0.000 title claims description 14
- -1 charge transport Substances 0.000 claims description 111
- 229920000642 polymer Polymers 0.000 claims description 111
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- 239000000463 material Substances 0.000 claims description 40
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- 238000000034 method Methods 0.000 claims description 38
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- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 239000000178 monomer Substances 0.000 claims description 34
- 238000013086 organic photovoltaic Methods 0.000 claims description 34
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- 238000004519 manufacturing process Methods 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
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- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 11
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- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
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- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 8
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 9
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
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- URMVZUQDPPDABD-UHFFFAOYSA-N thieno[2,3-f][1]benzothiole Chemical class C1=C2SC=CC2=CC2=C1C=CS2 URMVZUQDPPDABD-UHFFFAOYSA-N 0.000 description 8
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- 239000011541 reaction mixture Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
- 238000003618 dip coating Methods 0.000 description 6
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 6
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- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
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- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 4
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- VGCVJZVDAAWTFC-UHFFFAOYSA-N 4,7-dibromo-5,6-dioctoxy-2,1,3-benzothiadiazole Chemical compound BrC1=C(OCCCCCCCC)C(OCCCCCCCC)=C(Br)C2=NSN=C21 VGCVJZVDAAWTFC-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
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- JAHTUFOQIGLKFX-UHFFFAOYSA-N (3,7-diiodo-2-trimethylsilylthieno[2,3-f][1]benzothiol-6-yl)-trimethylsilane Chemical compound C1=C2C(I)=C([Si](C)(C)C)SC2=CC2=C1SC([Si](C)(C)C)=C2I JAHTUFOQIGLKFX-UHFFFAOYSA-N 0.000 description 2
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- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
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- ACUBGWMGURRCLC-UHFFFAOYSA-N 4,7-dibromo-5,6-dioctoxy-2,1,3-benzoxadiazole Chemical compound BrC1=C(OCCCCCCCC)C(OCCCCCCCC)=C(Br)C2=NON=C21 ACUBGWMGURRCLC-UHFFFAOYSA-N 0.000 description 2
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- 125000002958 pentadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 238000010189 synthetic method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- APBDREXAUGXCCV-UHFFFAOYSA-L tetraethylazanium;carbonate Chemical compound [O-]C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC APBDREXAUGXCCV-UHFFFAOYSA-L 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 1
- 125000004862 thiobutyl group Chemical group 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 1
- ZWUUZGAKKRHELQ-UHFFFAOYSA-N trimethyl-(2-thiophen-2-yl-2-trimethylstannyl-3h-thiophen-5-yl)stannane Chemical compound S1C([Sn](C)(C)C)=CCC1([Sn](C)(C)C)C1=CC=CS1 ZWUUZGAKKRHELQ-UHFFFAOYSA-N 0.000 description 1
- HDZULVYGCRXVNQ-UHFFFAOYSA-N trimethyl-(5-trimethylstannylthieno[3,2-b]thiophen-2-yl)stannane Chemical compound S1C([Sn](C)(C)C)=CC2=C1C=C([Sn](C)(C)C)S2 HDZULVYGCRXVNQ-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
-
- 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
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| PCT/EP2012/002626 WO2013010615A1 (en) | 2011-07-21 | 2012-06-21 | Conjugated polymers |
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| JP2014529350A JP2014529350A (ja) | 2014-11-06 |
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| JP6646649B2 (ja) * | 2014-10-22 | 2020-02-14 | レイナジー テック インコーポレイション | テルチオフェンをベースとする共役ポリマーおよびそれらの応用 |
| EP3235847B1 (en) * | 2014-12-19 | 2023-09-27 | LG Chem, Ltd. | Polymer and organic solar cell comprising same |
| CN105826472A (zh) * | 2016-05-16 | 2016-08-03 | 河南师范大学 | 一种有机光电开关及其制造方法和应用 |
| WO2017223407A1 (en) * | 2016-06-24 | 2017-12-28 | The Hong Kong University Of Science And Technology | Conjugated polymers containing alkyl and alkyl ester side chains |
| KR102074556B1 (ko) | 2017-03-06 | 2020-02-06 | 주식회사 엘지화학 | 중합체 및 이를 포함하는 유기 태양 전지 |
| KR102103059B1 (ko) * | 2017-05-18 | 2020-05-29 | 주식회사 엘지화학 | 유기트랜지스터 |
| KR102319359B1 (ko) * | 2017-10-13 | 2021-10-28 | 주식회사 엘지화학 | 유-무기 하이브리드 태양 전지 |
| WO2020018257A1 (en) * | 2018-07-16 | 2020-01-23 | Phillips 66 Company | Polymers containing 3'-(alkoxy)-[2,2'-bithiophene]-3carbonitrile for high performance organic photovoltaics |
| CN109243393B (zh) | 2018-10-29 | 2020-08-04 | 惠科股份有限公司 | 驱动电路及显示驱动装置 |
| US11600779B2 (en) * | 2019-08-27 | 2023-03-07 | Phillips 66 Company | Methods and systems of organic semiconducting polymers |
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| US5892244A (en) | 1989-01-10 | 1999-04-06 | Mitsubishi Denki Kabushiki Kaisha | Field effect transistor including πconjugate polymer and liquid crystal display including the field effect transistor |
| US5198153A (en) | 1989-05-26 | 1993-03-30 | International Business Machines Corporation | Electrically conductive polymeric |
| JP3224829B2 (ja) | 1991-08-15 | 2001-11-05 | 株式会社東芝 | 有機電界効果型素子 |
| WO1996021659A1 (en) | 1995-01-10 | 1996-07-18 | University Of Technology, Sydney | Organic semiconductor |
| EP0889350A1 (en) | 1997-07-03 | 1999-01-07 | ETHZ Institut für Polymere | Photoluminescent display devices (I) |
| US5998804A (en) | 1997-07-03 | 1999-12-07 | Hna Holdings, Inc. | Transistors incorporating substrates comprising liquid crystal polymers |
| ATE370176T1 (de) | 1999-03-05 | 2007-09-15 | Cambridge Display Tech Ltd | Polymerherstellung |
| AU777444B2 (en) | 1999-06-21 | 2004-10-14 | Flexenable Limited | Aligned polymers for an organic TFT |
| GB0028867D0 (en) | 2000-11-28 | 2001-01-10 | Avecia Ltd | Field effect translators,methods for the manufacture thereof and materials therefor |
| US20030021913A1 (en) | 2001-07-03 | 2003-01-30 | O'neill Mary | Liquid crystal alignment layer |
| DE10159946A1 (de) | 2001-12-06 | 2003-06-18 | Covion Organic Semiconductors | Prozess zur Herstellung von Aryl-Aryl gekoppelten Verbindungen |
| DE10241814A1 (de) | 2002-09-06 | 2004-03-25 | Covion Organic Semiconductors Gmbh | Prozeß zur Herstellung von Aryl-Aryl gekoppelten Verbindungen |
| DE10337077A1 (de) | 2003-08-12 | 2005-03-10 | Covion Organic Semiconductors | Konjugierte Copolymere, deren Darstellung und Verwendung |
| ATE452154T1 (de) * | 2003-10-15 | 2010-01-15 | Merck Patent Gmbh | Polybenzodithiophene |
| US7842942B2 (en) | 2003-11-28 | 2010-11-30 | Merck Patent Gmbh | Organic semiconducting layers |
| US8115200B2 (en) | 2007-12-13 | 2012-02-14 | E.I. Du Pont De Nemours And Company | Electroactive materials |
| JP2009215546A (ja) | 2008-02-13 | 2009-09-24 | Sumitomo Chemical Co Ltd | 多環縮環化合物、多環縮環重合体及びこれらを含む有機薄膜 |
| US8367798B2 (en) * | 2008-09-29 | 2013-02-05 | The Regents Of The University Of California | Active materials for photoelectric devices and devices that use the materials |
| JP5292514B2 (ja) | 2009-05-21 | 2013-09-18 | ポリエラ コーポレイション | 共役ポリマーおよび光電子デバイスにおけるその使用 |
| EP3134458B1 (en) | 2010-01-05 | 2023-11-01 | Raynergy Tek Inc. | Photovoltaic cell with benzodithiophene-containing polymer |
| US8304512B2 (en) | 2010-01-19 | 2012-11-06 | Xerox Corporation | Benzodithiophene based materials compositions |
| EP2856529A1 (en) * | 2012-06-05 | 2015-04-08 | Merck Patent GmbH | Small molecules and their use as organic semiconductors |
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| CN103687861B (zh) | 2017-08-25 |
| US9577197B2 (en) | 2017-02-21 |
| JP2014529350A (ja) | 2014-11-06 |
| TW201307433A (zh) | 2013-02-16 |
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