TWI665232B - 光電轉換元件以及使用於光電轉換元件之有機半導體化合物 - Google Patents
光電轉換元件以及使用於光電轉換元件之有機半導體化合物 Download PDFInfo
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- TWI665232B TWI665232B TW105103741A TW105103741A TWI665232B TW I665232 B TWI665232 B TW I665232B TW 105103741 A TW105103741 A TW 105103741A TW 105103741 A TW105103741 A TW 105103741A TW I665232 B TWI665232 B TW I665232B
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- photoelectric conversion
- conversion element
- type semiconductor
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- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002071 nanotube Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- BRVSNRNVRFLFLL-HQSVLGJOSA-N pcbo Chemical compound CCCCCCCCOC(=O)CCCC1([C@]23C4=C5C=CC6=C7C=CC8=C9C=CC%10=C%11C=CC%12=C(C=C4)[C@]31C1=C3C4=C2C5=C6C=2C7=C8C5=C9C%10=C(C3=C5C4=2)C%11=C%121)C1=CC=CC=C1 BRVSNRNVRFLFLL-HQSVLGJOSA-N 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ZKQGNWVXLNDTFA-UHFFFAOYSA-N trimethyl-(5-phenylthiophen-2-yl)stannane Chemical compound S1C([Sn](C)(C)C)=CC=C1C1=CC=CC=C1 ZKQGNWVXLNDTFA-UHFFFAOYSA-N 0.000 description 1
- DMTNYYLGEBSTEJ-UHFFFAOYSA-N triphenylene-1,2-diamine Chemical compound C1=CC=C2C3=C(N)C(N)=CC=C3C3=CC=CC=C3C2=C1 DMTNYYLGEBSTEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Photovoltaic Devices (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015-022034 | 2015-02-06 | ||
| JP2015022034 | 2015-02-06 |
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| TW201714911A TW201714911A (zh) | 2017-05-01 |
| TWI665232B true TWI665232B (zh) | 2019-07-11 |
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| TW108104817A TWI698457B (zh) | 2015-02-06 | 2016-02-04 | 高分子化合物 |
| TW105103741A TWI665232B (zh) | 2015-02-06 | 2016-02-04 | 光電轉換元件以及使用於光電轉換元件之有機半導體化合物 |
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| TW108104817A TWI698457B (zh) | 2015-02-06 | 2016-02-04 | 高分子化合物 |
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| JP (1) | JP6642455B2 (ja) |
| TW (2) | TWI698457B (ja) |
| WO (1) | WO2016125822A1 (ja) |
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| US20190088891A1 (en) * | 2016-03-15 | 2019-03-21 | Merck Patent Gmbh | Organic semiconductors |
| JP7468346B2 (ja) * | 2019-04-26 | 2024-04-16 | 東洋紡株式会社 | 高分子化合物 |
| JP6798651B1 (ja) * | 2019-04-26 | 2020-12-09 | 東洋紡株式会社 | 高分子化合物 |
| JP7480705B2 (ja) | 2019-06-17 | 2024-05-10 | 東洋紡株式会社 | 光電変換素子 |
| JP6934989B2 (ja) * | 2019-08-29 | 2021-09-15 | 住友化学株式会社 | 有機光電変換材料 |
| US20220310939A1 (en) * | 2019-08-29 | 2022-09-29 | Sumitomo Chemical Company, Limited | Organic photoelectric conversion material |
| CN111518548A (zh) * | 2020-07-05 | 2020-08-11 | 杭州纤纳光电科技有限公司 | 一种光下转换材料及制备方法和光下转换胶膜及光伏组件 |
| CN114031627B (zh) * | 2020-10-26 | 2023-04-25 | 广东聚华印刷显示技术有限公司 | 可交联化合物和其制备方法及电子传输材料和发光二极管 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007238530A (ja) * | 2006-03-10 | 2007-09-20 | Central Glass Co Ltd | ベンゾビスアゾール骨格をもつ有機π電子系材料およびその製造方法 |
| TW201002722A (en) * | 2008-01-22 | 2010-01-16 | Ricoh Co Ltd | Benzobisthiazole compound, benzobisthiazole polymer, organic film including the compound or polymer and transistor including the organic film |
| TW201139503A (en) * | 2009-10-28 | 2011-11-16 | Univ Washington | Copolymer semiconductors comprising thiazolothiazole or benzobisthiazole, or benzobisoxazole electron acceptor subunits, and electron donor subunits, and their uses in transistors and solar cells |
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| JPWO2010001754A1 (ja) * | 2008-06-30 | 2011-12-15 | 東洋紡績株式会社 | プリント配線基板用プリプレグおよびプリント配線基板 |
| US9023964B2 (en) * | 2013-03-13 | 2015-05-05 | Iowa State University Research Foundation, Inc. | Conjugated polymer and semiconductor devices including the same |
| JP6500786B2 (ja) * | 2014-02-14 | 2019-04-17 | 東洋紡株式会社 | 有機半導体材料 |
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2016
- 2016-02-03 WO PCT/JP2016/053188 patent/WO2016125822A1/ja active Application Filing
- 2016-02-03 JP JP2016573397A patent/JP6642455B2/ja active Active
- 2016-02-04 TW TW108104817A patent/TWI698457B/zh active
- 2016-02-04 TW TW105103741A patent/TWI665232B/zh active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007238530A (ja) * | 2006-03-10 | 2007-09-20 | Central Glass Co Ltd | ベンゾビスアゾール骨格をもつ有機π電子系材料およびその製造方法 |
| TW201002722A (en) * | 2008-01-22 | 2010-01-16 | Ricoh Co Ltd | Benzobisthiazole compound, benzobisthiazole polymer, organic film including the compound or polymer and transistor including the organic film |
| TW201139503A (en) * | 2009-10-28 | 2011-11-16 | Univ Washington | Copolymer semiconductors comprising thiazolothiazole or benzobisthiazole, or benzobisoxazole electron acceptor subunits, and electron donor subunits, and their uses in transistors and solar cells |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI698457B (zh) | 2020-07-11 |
| TW201920347A (zh) | 2019-06-01 |
| TW201714911A (zh) | 2017-05-01 |
| JPWO2016125822A1 (ja) | 2017-11-16 |
| WO2016125822A1 (ja) | 2016-08-11 |
| JP6642455B2 (ja) | 2020-02-05 |
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