CN105609662A - 一种钙钛矿光伏材料专用的空穴传输材料的制备方法 - Google Patents
一种钙钛矿光伏材料专用的空穴传输材料的制备方法 Download PDFInfo
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- CN105609662A CN105609662A CN201510966209.8A CN201510966209A CN105609662A CN 105609662 A CN105609662 A CN 105609662A CN 201510966209 A CN201510966209 A CN 201510966209A CN 105609662 A CN105609662 A CN 105609662A
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- 239000000463 material Substances 0.000 title claims abstract description 82
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 230000005525 hole transport Effects 0.000 title abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 50
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims abstract description 18
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 claims abstract description 14
- HEYWYQQFXVEUSH-UHFFFAOYSA-N 2,7-dichlorofluoren-9-one Chemical compound C1=C(Cl)C=C2C(=O)C3=CC(Cl)=CC=C3C2=C1 HEYWYQQFXVEUSH-UHFFFAOYSA-N 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
- 238000000967 suction filtration Methods 0.000 claims description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 22
- 238000010438 heat treatment Methods 0.000 claims description 17
- 238000005406 washing Methods 0.000 claims description 17
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000002386 leaching Methods 0.000 claims description 8
- 235000011056 potassium acetate Nutrition 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- AIGRXSNSLVJMEA-FQEVSTJZSA-N ethoxy-(4-nitrophenoxy)-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound O([P@@](=S)(OCC)C=1C=CC=CC=1)C1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-FQEVSTJZSA-N 0.000 claims description 6
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 4
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 2
- 229940070765 laurate Drugs 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 claims 1
- -1 siloxane structures Chemical group 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 2
- AZSSGWNYBQGDJL-UHFFFAOYSA-N B1BBBB1 Chemical compound B1BBBB1 AZSSGWNYBQGDJL-UHFFFAOYSA-N 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000006617 triphenylamine group Chemical group 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 19
- 238000001816 cooling Methods 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 3
- 241000790917 Dioxys <bee> Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- YSGZPEILUZVKDO-UHFFFAOYSA-N [F].C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 Chemical group [F].C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 YSGZPEILUZVKDO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- SLDBAXYJAIRQMX-UHFFFAOYSA-N 3-ethylthiophene Chemical compound CCC=1C=CSC=1 SLDBAXYJAIRQMX-UHFFFAOYSA-N 0.000 description 1
- RLAZRBVKESZVAD-UHFFFAOYSA-N C(CCC)[Sn]CCCC.C(C=CC1=CC=CC=C1)(=O)O Chemical compound C(CCC)[Sn]CCCC.C(C=CC1=CC=CC=C1)(=O)O RLAZRBVKESZVAD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- YSZKDKZFYUOELW-UHFFFAOYSA-N [diphenyl-(4-propan-2-ylcyclohexyl)methyl]benzene Chemical compound C1(=CC=CC=C1)C(C1CCC(CC1)C(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 YSZKDKZFYUOELW-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- HODFCFXCOMKRCG-UHFFFAOYSA-N bitolterol mesylate Chemical compound CS([O-])(=O)=O.C1=CC(C)=CC=C1C(=O)OC1=CC=C(C(O)C[NH2+]C(C)(C)C)C=C1OC(=O)C1=CC=C(C)C=C1 HODFCFXCOMKRCG-UHFFFAOYSA-N 0.000 description 1
- AOWKSNWVBZGMTJ-UHFFFAOYSA-N calcium titanate Chemical compound [Ca+2].[O-][Ti]([O-])=O AOWKSNWVBZGMTJ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 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
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005259 triarylamine group Chemical group 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
- H10K85/115—Polyfluorene; Derivatives thereof
-
- 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
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Photovoltaic Devices (AREA)
Abstract
Description
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CN201510966209.8A CN105609662B (zh) | 2015-12-22 | 2015-12-22 | 一种钙钛矿光伏材料专用的空穴传输材料的制备方法 |
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CN201510966209.8A CN105609662B (zh) | 2015-12-22 | 2015-12-22 | 一种钙钛矿光伏材料专用的空穴传输材料的制备方法 |
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CN105609662A true CN105609662A (zh) | 2016-05-25 |
CN105609662B CN105609662B (zh) | 2017-12-12 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108365103A (zh) * | 2018-02-22 | 2018-08-03 | 南京工业大学 | 一种含硼空穴掺杂剂在钙钛矿太阳能电池空穴传输层中的应用 |
CN113388104A (zh) * | 2021-07-02 | 2021-09-14 | 黑龙江大学 | 含有芴基与三苯胺直接键连的三芳胺类聚酰胺及其制备方法和应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1835926A (zh) * | 2003-06-17 | 2006-09-20 | 詹森药业有限公司 | 非肽类取代螺苯并氮杂䓬衍生物的制备方法 |
WO2015041428A1 (ko) * | 2013-09-17 | 2015-03-26 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치 |
CN104485424A (zh) * | 2013-12-02 | 2015-04-01 | 南洋理工大学 | 空穴传输分子及其在太阳能电池中的用途 |
CN105006522A (zh) * | 2015-06-19 | 2015-10-28 | 苏州大学 | 一种基于钙钛矿的倒置薄膜太阳能电池及其制备方法 |
CN105037179A (zh) * | 2015-05-29 | 2015-11-11 | 中山大学 | 一种新型空穴传输材料及其制备方法和应用 |
-
2015
- 2015-12-22 CN CN201510966209.8A patent/CN105609662B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1835926A (zh) * | 2003-06-17 | 2006-09-20 | 詹森药业有限公司 | 非肽类取代螺苯并氮杂䓬衍生物的制备方法 |
WO2015041428A1 (ko) * | 2013-09-17 | 2015-03-26 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치 |
CN104485424A (zh) * | 2013-12-02 | 2015-04-01 | 南洋理工大学 | 空穴传输分子及其在太阳能电池中的用途 |
CN105037179A (zh) * | 2015-05-29 | 2015-11-11 | 中山大学 | 一种新型空穴传输材料及其制备方法和应用 |
CN105006522A (zh) * | 2015-06-19 | 2015-10-28 | 苏州大学 | 一种基于钙钛矿的倒置薄膜太阳能电池及其制备方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108365103A (zh) * | 2018-02-22 | 2018-08-03 | 南京工业大学 | 一种含硼空穴掺杂剂在钙钛矿太阳能电池空穴传输层中的应用 |
CN113388104A (zh) * | 2021-07-02 | 2021-09-14 | 黑龙江大学 | 含有芴基与三苯胺直接键连的三芳胺类聚酰胺及其制备方法和应用 |
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CN105609662B (zh) | 2017-12-12 |
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