NL2014097B1 - Hole transport azomethine molecule. - Google Patents

Hole transport azomethine molecule. Download PDF

Info

Publication number: NL2014097B1
Authority: NL; Netherlands
Prior art keywords: layer; molecule; photovoltaic device; hole transport; azomethine
Prior art date: 2015-01-08

Application number

NL2014097A

Other languages

English (en)

Dutch (nl)

Other versions

NL2014097A (en

Inventor

Leonardus Petrus Michiel

Jacobus Dingemans Theodorus

Original Assignee

Univ Delft Tech

Priority date (The priority date 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 date listed.)

2015-01-08

Filing date

2015-01-08

Publication date

2016-09-30

2015-01-08 Application filed by Univ Delft Tech filed Critical Univ Delft Tech

2015-01-08 Priority to NL2014097A priority Critical patent/NL2014097B1/en

2016-01-07 Priority to PCT/NL2016/050007 priority patent/WO2016111623A1/fr

2016-09-23 Publication of NL2014097A publication Critical patent/NL2014097A/en

2016-09-30 Application granted granted Critical

2016-09-30 Publication of NL2014097B1 publication Critical patent/NL2014097B1/en

Links

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238000004949 mass spectrometry Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
LLWRXQXPJMPHLR-UHFFFAOYSA-N methylazanium;iodide Chemical compound [I-].[NH3+]C LLWRXQXPJMPHLR-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
238000000399 optical microscopy Methods 0.000 description 1
230000005693 optoelectronics Effects 0.000 description 1
238000013086 organic photovoltaic Methods 0.000 description 1
UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 1
VXTFGYMINLXJPW-UHFFFAOYSA-N phosphinane Chemical compound C1CCPCC1 VXTFGYMINLXJPW-UHFFFAOYSA-N 0.000 description 1
UNQNIRQQBJCMQR-UHFFFAOYSA-N phosphorine Chemical compound C1=CC=PC=C1 UNQNIRQQBJCMQR-UHFFFAOYSA-N 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000007639 printing Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
238000011160 research Methods 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
238000012995 silicone-based technology Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
238000002207 thermal evaporation Methods 0.000 description 1
NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 1
JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 description 1
BISQTCXKVNCDDA-UHFFFAOYSA-N thiepine Chemical compound S1C=CC=CC=C1 BISQTCXKVNCDDA-UHFFFAOYSA-N 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
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 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/10—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising heterojunctions between organic semiconductors and inorganic semiconductors
- 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
- H10K85/50—Organic perovskites; Hybrid organic-inorganic perovskites [HOIP], e.g. CH3NH3PbI3
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- 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)
Physics & Mathematics (AREA)
Spectroscopy & Molecular Physics (AREA)
Inorganic Chemistry (AREA)
Electromagnetism (AREA)
Photovoltaic Devices (AREA)

NL2014097A 2015-01-08 2015-01-08 Hole transport azomethine molecule. NL2014097B1 (en)

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NL2014097A NL2014097B1 (en)	2015-01-08	2015-01-08	Hole transport azomethine molecule.
PCT/NL2016/050007 WO2016111623A1 (fr)	2015-01-08	2016-01-07	Molécule d'azométhine à transport de trous

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NL2014097A NL2014097B1 (en)	2015-01-08	2015-01-08	Hole transport azomethine molecule.

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CN107275487B (zh) *	2017-06-08	2019-04-30	华东师范大学	一种高效稳定的钙钛矿太阳能电池及其制备方法
CN107785487A (zh) *	2017-10-31	2018-03-09	南京旭羽睿材料科技有限公司	一种石墨烯薄膜太阳能电池及其制备方法
CN108054279B (zh) *	2017-12-07	2021-06-11	暨南大学	Fk102配体修饰的钙钛矿型太阳能电池及其钙钛矿层的制备方法
CN108682747B (zh) *	2018-05-16	2020-11-24	西安电子科技大学	一种双异质结钙钛矿光电器件及其制备方法
JP7319508B2 (ja)	2018-11-30	2023-08-02	日亜化学工業株式会社	セラミックス焼結体の製造方法、セラミックス焼結体及び発光装置
CN115440889B (zh) *	2022-09-06	2025-12-16	华中科技大学鄂州工业技术研究院	一种提高钙钛矿太阳能电池效率和稳定性的方法及钙钛矿太阳能电池

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- 2015-01-08 NL NL2014097A patent/NL2014097B1/en not_active IP Right Cessation
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Also Published As

Publication number	Publication date
NL2014097A (en)	2016-09-23
WO2016111623A1 (fr)	2016-07-14

Publication	Publication Date	Title
Farokhi et al.	2022	The evolution of triphenylamine hole transport materials for efficient perovskite solar cells
Fu et al.	2022	Multifunctional two-dimensional polymers for perovskite solar cells with efficiency exceeding 24%
Zhang et al.	2018	Recent advance in solution‐processed organic interlayers for high‐performance planar perovskite solar cells
Rakstys et al.	2019	Efficiency vs. stability: dopant-free hole transporting materials towards stabilized perovskite solar cells
Zhang et al.	2020	A review on solution‐processable dopant‐free small molecules as hole‐transporting materials for efficient perovskite solar cells
Meng et al.	2022	Configurable organic charge carriers toward stable perovskite photovoltaics
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Teh et al.	2016	A review of organic small molecule-based hole-transporting materials for meso-structured organic–inorganic perovskite solar cells
Chou et al.	2016	Zinc porphyrin–ethynylaniline conjugates as novel hole-transporting materials for perovskite solar cells with power conversion efficiency of 16.6%
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Lin et al.	2019	Donor–acceptor–donor type cyclopenta [2, 1-b; 3, 4-b′] dithiophene derivatives as a new class of hole transporting materials for highly efficient and stable perovskite solar cells
Dhingra et al.	2016	Hole‐transporting materials for perovskite‐sensitized solar cells
US20160351342A1 (en)	2016-12-01	Hole transporting and light absorbing material for solid state solar cells
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Wang et al.	2022	Constructing efficient hole-transporting materials by tuning fluorine substitution for inverted perovskite solar cells with efficiency exceeding 20%
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Chang et al.	2024	Enhancing efficiency and stability in perovskite solar cells through blended hole transporting materials incorporating benzo [g] quinoxaline-conjugated small molecules
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Jia et al.	2022	Fluorination of carbazole-based polymeric hole-transporting material improves device performance of perovskite solar cells with fill factor up to 82%
NL2012451B1 (en)	2016-01-08	Small azomethine molecule.
Yang et al.	2025	Molecular Si-Cyclization Enables Versatile Organic Semiconductors for Durable Perovskite Solar Cells with 24.8% Efficiency
Liu et al.	2023	Exploration of the effect of fluoridation on the doping-free linear dibenzothiophene-based hole-transport material applied for inverted perovskite solar cells

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