A kind of asymmetric porphyrin organic small molecule cathode interface material and its preparation method and application

A cathode interface and small molecule technology, which is applied in the fields of organic chemistry, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problem of little research on asymmetric porphyrin cathode interface materials, so as to improve photoelectric conversion efficiency and improve Current, the effect of increasing the π-conjugate length

Inactive Publication Date: 2020-01-14
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the good light absorption of porphyrin compounds, they are generally used as the active layer of organic solar cells. Although porphyrins are also used in the cathode interface, most of them are symmetric porphyrin interface materials, and asymmetric porphyrin cathode interface materials are rarely studied.

Method used

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  • A kind of asymmetric porphyrin organic small molecule cathode interface material and its preparation method and application
  • A kind of asymmetric porphyrin organic small molecule cathode interface material and its preparation method and application
  • A kind of asymmetric porphyrin organic small molecule cathode interface material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Synthesis of 5,15-bis(5-isooctylthiophene)porphyrin

[0042]

[0043] In a 1L three-neck round bottom flask, add 2-isooctyl-5-carbaldehydethiophene (2.24g, 10mmol), bipyrromethane (1.46g, 10mmol) and 600mL dichloromethane, exhaust with nitrogen for 30 minutes, then add 0.12mL of trifluoroacetic acid, stirred and reacted at room temperature for 12 hours, then added 1.89g of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), continued to stir and reacted for 12 hours, and ended the reaction. Using silica gel column chromatography, dichloromethane was used as eluent, spin-dried to obtain the crude product, and then recrystallized with chloroform / methanol to obtain a dark red solid. The NMR data of the red solid are: 1 H NMR (500MHz, Chloroform-d) δ / ppm 10.28(s, 2H), 9.38(d, J=4.6Hz, 4H), 9.35(d, J=4.6Hz, 4H), 7.74(d, J=3.3 Hz,2H),7.22–7.20(m,2H),3.12–3.09(m,4H),1.38–1.18(m,18H),1.08(t,J=7.4Hz,6H),1.01(t,J= 7.1Hz, 6H), -2.96(s, 2H).

[0044] (2) Synthesis of 5-bromo-...

Embodiment 2

[0063] 5-triisopropylsilylacetylene-15-(9,9-bis(3'-(N,N-dimethyl-N-ethylammonium bromide)propyl)fluorene-2-acetylene)-10, Synthesis of 20-bis(5-isooctylthiophene) zinc porphyrin

[0064]

[0065] Add 5-triisopropylsilylacetylene-15-(9,9-bis(3'-(N,N-dimethylamino)propyl)fluorene-2-acetylene)-10,20 into a 50mL two-necked flask - Bis(5-isooctylthiophene) zinc porphyrin (50mg, 0.038mmol) and N,N-dimethylformamide 1ml and 1ml tetrahydrofuran, stir to dissolve and add bromoethane 1ml, heat to 60°C and keep it The temperature was reacted for 12 hours, the reaction was completed, and the product was obtained by centrifugation. Mass(MALDI-TOF): Obs.1517.8; Calcd.for C 84 h 108 N 6 Br 2 S 2 SiZn, 1519.2.

[0066] The asymmetric porphyrin organic small molecule cathode interface material prepared in this example was dissolved in methanol, and the ultraviolet-visible absorption spectrum of the obtained methanol dilute solution was as follows: figure 2 .

[0067] The asymmetri...

Embodiment 3

[0070] (1) 5-ethyne-15-(9,9-bis(3'-(N,N-dimethylamino)propyl)fluorene-2-ethyne)-10,20-bis(5-isooctyl Synthesis of thiophene) zinc porphyrin

[0071]

[0072] Add 5-triisopropylsilylacetylene-15-(9,9-bis(3'-(N,N-dimethylamino)propyl)fluorene-2-acetylene)-10,20 to a 100mL one-necked flask - Bis(5-isooctylthiophene) zinc porphyrin (91mg, 0.07mmol) and 20ml tetrahydrofuran were stirred and dissolved, and 0.07ml of 1mol / L tetrabutylammonium fluoride (TBAF) tetrahydrofuran solution was added, and stirred at room temperature for 5min, After the reaction was completed, it was extracted with chloroform and spin-dried to obtain the product.

[0073] (2) 5-(9,9-bis(3'-(N,N-dimethylamino)propyl)fluorene-2-ethyne)-15-(3-(2-thiophene)-2,5 -Bis(2-ethylhexyl)-6-(2-thiophene)pyrrole[3,4-c]pyrrole-1,4(2H,5H)-dione)-10,20-bis(5-isooctyl Synthesis of thiophene) zinc porphyrin

[0074]

[0075]5-ethyne-15-(9,9-bis(3'-(N,N-dimethylamino)propyl)fluorene-2-ethyne)-10,20-bis(5-isooctylthioph...

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Abstract

The invention relates to the field of organic solar cell cathode interface materials, and discloses an asymmetric porphyrin organic small molecule cathode interface material, a preparation method and application thereof. The asymmetric porphyrin organic small molecule has a porphyrin ring as the core, and a group is respectively connected to the four meso positions of the porphyrin ring, one of which is a conjugated unit with a polar group, and one is an electron-withdrawing or donating unit. Conjugated units for electrons, and the other two are aromatic groups substituted by alkyl chains. The asymmetric porphyrin organic small molecule cathode interface material of the present invention improves the solubility in methanol, which is beneficial to the preparation of organic solar cells; adjusts the energy level of the molecule, improves the electron transport performance; improves the surface morphology, improves the Battery performance, using the material of the invention can further improve the photovoltaic performance of organic solar cells.

Description

technical field [0001] The invention relates to the field of organic photovoltaic materials, in particular to an asymmetric porphyrin organic small molecule cathode interface material and its preparation method and application. Background technique [0002] The use of solar energy is one of the ways to alleviate the upcoming energy crisis. At present, the theoretically mature way of utilizing solar energy is the crystalline silicon semiconductor solar cell in the inorganic field. Although the crystalline silicon semiconductor solar cell has been commercialized, the hardness and melting point of crystalline silicon are low. High, a lot of energy is consumed in the processing process, which makes the processing cost higher, so its application is also limited. Compared with crystalline silicon solar cells, organic solar cells have the advantages of low cost, flexibility, light weight, and large-area production, and are favored by researchers. [0003] Organic solar cells usual...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C07F7/10C07D519/00H01L51/46H01L51/42
CPCC07D487/22C07D519/00C07F7/10H10K85/381H10K30/00Y02E10/549
Inventor 彭小彬邓科陈学彬刘勇郑何敏祝蓓周莹
Owner SOUTH CHINA UNIV OF TECH
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