CN102617525A - 一类用于全固态量子点敏化太阳能电池的杂环修饰的三苯胺有机空穴传输材料 - Google Patents
一类用于全固态量子点敏化太阳能电池的杂环修饰的三苯胺有机空穴传输材料 Download PDFInfo
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- CN102617525A CN102617525A CN2012100522587A CN201210052258A CN102617525A CN 102617525 A CN102617525 A CN 102617525A CN 2012100522587 A CN2012100522587 A CN 2012100522587A CN 201210052258 A CN201210052258 A CN 201210052258A CN 102617525 A CN102617525 A CN 102617525A
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- Prior art keywords
- triphenylamine
- quantum dot
- transport material
- hole transport
- organic hole
- 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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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 239000000463 material Substances 0.000 title claims abstract description 56
- 239000002096 quantum dot Substances 0.000 title claims abstract description 53
- 230000005525 hole transport Effects 0.000 title claims abstract description 44
- 239000007787 solid Substances 0.000 title claims abstract description 28
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 24
- 230000004048 modification Effects 0.000 title claims abstract description 15
- 238000012986 modification Methods 0.000 title claims abstract description 15
- 206010070834 Sensitisation Diseases 0.000 title abstract description 6
- 230000008313 sensitization Effects 0.000 title abstract description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 96
- 150000002240 furans Chemical class 0.000 claims abstract description 42
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 229930192474 thiophene Natural products 0.000 claims description 40
- -1 compound furans Chemical class 0.000 claims description 31
- 150000003233 pyrroles Chemical class 0.000 claims description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 238000004528 spin coating Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 150000001651 triphenylamine derivatives Chemical class 0.000 abstract description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 10
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 abstract 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 230000002349 favourable effect Effects 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 239000011159 matrix material Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 19
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000001246 bromo group Chemical group Br* 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229960001866 silicon dioxide Drugs 0.000 description 8
- 239000004408 titanium dioxide Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 125000006617 triphenylamine group Chemical class 0.000 description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011244 liquid electrolyte Substances 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 1
- OTZWITHPRWRMMX-UHFFFAOYSA-N 2-butyl-1h-pyrrole Chemical class CCCCC1=CC=CN1 OTZWITHPRWRMMX-UHFFFAOYSA-N 0.000 description 1
- NWZIYQNUCXUJJJ-UHFFFAOYSA-N 2-butylfuran Chemical class CCCCC1=CC=CO1 NWZIYQNUCXUJJJ-UHFFFAOYSA-N 0.000 description 1
- BMBKXWCUKZCDCT-UHFFFAOYSA-N 2-butylselenophene Chemical compound C(CCC)C=1[Se]C=CC1 BMBKXWCUKZCDCT-UHFFFAOYSA-N 0.000 description 1
- MNDZHERKKXUTOE-UHFFFAOYSA-N 2-butylthiophene Chemical compound CCCCC1=CC=CS1 MNDZHERKKXUTOE-UHFFFAOYSA-N 0.000 description 1
- RXEIUHSMORSJCK-UHFFFAOYSA-N 2-methylselenophene Chemical compound CC1=CC=C[se]1 RXEIUHSMORSJCK-UHFFFAOYSA-N 0.000 description 1
- FEKWWZCCJDUWLY-UHFFFAOYSA-N 3-methyl-1h-pyrrole Chemical compound CC=1C=CNC=1 FEKWWZCCJDUWLY-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000003837 high-temperature calcination Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
Images
Classifications
-
- 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
- Photovoltaic Devices (AREA)
- Hybrid Cells (AREA)
Abstract
Description
一取代 | 二取代 | 三取代 | |
呋喃 | 1.6% | 1.9% | 1.7% |
噻吩 | 1.5% | 1.2% | 1.7% |
硒吩 | 1.5% | 1.4% | 1.9% |
吡咯 | 1.7% | 1.6% | 1.3% |
一取代 | 二取代 | 三取代 | |
5-甲基呋喃 | 1.6% | 1.8% | 1.6% |
5-丁基呋喃 | 1.5% | 1.9% | 1.8% |
5-辛基呋喃 | 1.3% | 1.4% | 1.7% |
5-氧辛基呋喃 | 1.8% | 1.9% | 1.8% |
5-甲基噻吩 | 1.1% | 1.8% | 1.7% |
5-丁基噻吩 | 1.2% | 1.8% | 1.6% |
5-辛基噻吩 | 1.8% | 1.1% | 1.6% |
5-氧辛基噻吩 | 1.9% | 1.5% | 1.8% |
5-甲基硒吩 | 1.4% | 1.4% | 1.7% |
5-丁基硒吩 | 1.2% | 1.0% | 1.9% |
5-辛基硒吩 | 2.4% | 1.5% | 1.8% |
5-氧辛基硒吩 | 1.7% | 1.8% | 1.9% |
5-甲基吡咯 | 2.2% | 2.3% | 1.5% |
5-丁基吡咯 | 1.7% | 1.8% | 1.7% |
5-辛基吡咯 | 1.3% | 1.2% | 1.5% |
5-氧辛基吡咯 | 1.6% | 1.7% | 1.9% |
Claims (6)
Priority Applications (1)
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CN201210052258.7A CN102617525B (zh) | 2012-03-02 | 2012-03-02 | 一类用于全固态量子点敏化太阳能电池的杂环修饰的三苯胺有机空穴传输材料 |
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CN201210052258.7A CN102617525B (zh) | 2012-03-02 | 2012-03-02 | 一类用于全固态量子点敏化太阳能电池的杂环修饰的三苯胺有机空穴传输材料 |
Publications (2)
Publication Number | Publication Date |
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CN102617525A true CN102617525A (zh) | 2012-08-01 |
CN102617525B CN102617525B (zh) | 2014-02-26 |
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CN201210052258.7A Expired - Fee Related CN102617525B (zh) | 2012-03-02 | 2012-03-02 | 一类用于全固态量子点敏化太阳能电池的杂环修饰的三苯胺有机空穴传输材料 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019093395A1 (ja) * | 2017-11-07 | 2019-05-16 | 国立大学法人京都大学 | 分子設計方法、プログラム、ホスト材料、発光分子および有機発光素子 |
CN111116544A (zh) * | 2018-10-30 | 2020-05-08 | 东泰高科装备科技有限公司 | 有机空穴传输材料、其制备方法及其应用 |
CN111233824A (zh) * | 2018-11-28 | 2020-06-05 | 东泰高科装备科技有限公司 | 有机光谱转换材料、其制备方法及包含其的发光太阳能聚光器 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070028962A1 (en) * | 2005-08-08 | 2007-02-08 | Samsung Electronics Co., Ltd. | Low molecular weight conjugated nitrogen compounds and devices fabricated using the same |
EP1767608A1 (en) * | 2005-09-27 | 2007-03-28 | Samsung Electronics Co., Ltd. | Tris(thienylphenyl)amine derivatives as organic semiconductors |
US20080178933A1 (en) * | 2007-01-31 | 2008-07-31 | Konica Minolta Business Technologies, Inc. | Photoelectric conversion element and solar cell |
CN101525334A (zh) * | 2009-04-13 | 2009-09-09 | 江南大学 | 一种有机太阳能电池材料及其制备 |
-
2012
- 2012-03-02 CN CN201210052258.7A patent/CN102617525B/zh not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070028962A1 (en) * | 2005-08-08 | 2007-02-08 | Samsung Electronics Co., Ltd. | Low molecular weight conjugated nitrogen compounds and devices fabricated using the same |
EP1767608A1 (en) * | 2005-09-27 | 2007-03-28 | Samsung Electronics Co., Ltd. | Tris(thienylphenyl)amine derivatives as organic semiconductors |
US20080178933A1 (en) * | 2007-01-31 | 2008-07-31 | Konica Minolta Business Technologies, Inc. | Photoelectric conversion element and solar cell |
CN101525334A (zh) * | 2009-04-13 | 2009-09-09 | 江南大学 | 一种有机太阳能电池材料及其制备 |
Non-Patent Citations (4)
Title |
---|
AKINORI SAEKI,等: "Long-Lived Hole Stabilized at a Triphenylamine Core and Shielded by Rigid Phenylazomethine Dendrons: A Pulse Radiolysis Study", 《J. PHYS. CHEM. B》, vol. 112, no. 49, 13 November 2008 (2008-11-13) * |
ANTONIO CRAVINO,等: "A star-shaped triphenylamine p-conjugated system with internal charge-transfer as donor material for hetero-junction solar cells", 《CHEM. COMMUN.》, 21 February 2006 (2006-02-21) * |
JEREMY T. KEARNS 等: "Enhanced performance of triarylamine redox electrodes through directed electrochemical polymerization", 《J. MATER. CHEM.》, vol. 22, 23 December 2011 (2011-12-23), pages 2392 - 2394 * |
VENKATAKRISHNAN PARTHASARATHY,等: "Dipolar versus Octupolar Triphenylamine-Based Fluorescent Organic Nanoparticles as Brilliant One- and Two-Photon Emitters for (Bio)imaging", 《SMALL》, vol. 7, no. 22, 31 December 2011 (2011-12-31) * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019093395A1 (ja) * | 2017-11-07 | 2019-05-16 | 国立大学法人京都大学 | 分子設計方法、プログラム、ホスト材料、発光分子および有機発光素子 |
CN111116544A (zh) * | 2018-10-30 | 2020-05-08 | 东泰高科装备科技有限公司 | 有机空穴传输材料、其制备方法及其应用 |
CN111233824A (zh) * | 2018-11-28 | 2020-06-05 | 东泰高科装备科技有限公司 | 有机光谱转换材料、其制备方法及包含其的发光太阳能聚光器 |
CN111233824B (zh) * | 2018-11-28 | 2022-09-09 | 紫石能源有限公司 | 有机光谱转换材料、其制备方法及包含其的发光太阳能聚光器 |
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CN102617525B (zh) | 2014-02-26 |
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Inventor after: Li Chunsheng Inventor after: Sun Yan Inventor after: Shi Jifu Inventor after: Ma Xuegang Inventor after: Yao Weixue Inventor after: Xu Liangshi Inventor after: Wang Yaozu Inventor after: Wang Lina Inventor before: Li Chunsheng Inventor before: Sun Yan Inventor before: Shi Jifu Inventor before: Wang Yaozu Inventor before: Wang Lina Inventor before: Ma Xuegang |
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Free format text: CORRECT: INVENTOR; FROM: LI CHUNSHENG SUN YAN SHI JIFU WANG YAOZU WANG LINA MA XUEGANG TO: LI CHUNSHENG SUN YAN SHI JIFU MA XUEGANG YAO WEIXUE XU LIANGSHI WANG YAOZU WANG LINA |
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