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Preparation of cross-linked electrode modification materials by ethylenic bond-mercapto click chemistry and its application in organic electronic devices

A technology of electrode modification and chemical method, which is applied in the field of polymer optoelectronic materials and devices, can solve the problems of high raw material cost, pollution, and high energy consumption, and achieve the goals of improving work function, good resistance to solvent elution, and improving device performance Effect

Active Publication Date: 2018-05-15
中山市东石材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Inorganic solar cells represented by inorganic silicon have been relatively maturely applied in the market, but there are many problems in the production process, such as high energy consumption, high cost of raw materials, and serious pollution.

Method used

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  • Preparation of cross-linked electrode modification materials by ethylenic bond-mercapto click chemistry and its application in organic electronic devices
  • Preparation of cross-linked electrode modification materials by ethylenic bond-mercapto click chemistry and its application in organic electronic devices
  • Preparation of cross-linked electrode modification materials by ethylenic bond-mercapto click chemistry and its application in organic electronic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthetic route of the representative cross-linkable conjugated polymer PFN-V containing ethylenic groups in the side chain is as follows:

[0041]

[0042] (1) Preparation of monomer 2

[0043] Add 6.48g (20mmol) dibromofluorene and 540mg (0.22mmol) tetrabutylammonium bromide in a 250mL three-necked flask with a stirring bar, add 75mL toluene solution and 75mL mass fraction of 50% sodium hydroxide solution, After stirring for 5 minutes, 90mL (50mmol) 6-bromo-1-hexene was slowly added dropwise, and the reaction was refluxed for 17h. The reaction solution was extracted with water and ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, and suction filtered. After the obtained filtrate was rotary evaporated, it was passed through a column with petroleum ether as the eluent, and the final product was white crystals. 1 HNMR (500MHz, CDCl3, δ, ppm): 7.52‐7.48 (d, 2H), 7.47‐7.41 (d, 4Hz), 5.66‐5.56 (m, 2H), 4.89‐4.81 (t, 4H, J=18Hz) ,1.96‐1.89...

Embodiment 2

[0050] Taking the polymer PFN-V as an example to illustrate that this kind of polymer has the performance of anti-solvent elution after cross-linking treatment

[0051] The polymer PFN-V synthesized in Example 1 was dissolved in chloroform, then 77% of 1,8-octanedithiol was added, the solution was filtered with a 0.45 micron filter membrane, and spin-coated on a quartz plate to form a film with a thickness of about 20 nanometers. Measure the absorbance of PFN-V after film formation with a UV tester (HP 8453 spectrophotometer) produced by Hewlett-Packard Company, corresponding to figure 2 Curve 1. Afterwards, the PFN-V film is irradiated with ultraviolet light with a wavelength of 365 nm to form an insoluble cross-linked film. The cross-linked PFN-V film was soaked in chloroform pure solvent.

[0052] The absorbance of the cross-linked PFN-V after being washed with chloroform was measured by UV test, corresponding to figure 2 Curve 3 in, from which we can see the crosslin...

Embodiment 3

[0054] The cross-linked conjugated polymer PFN-V synthesized in Example 2 is used as a cathode interface modification in an inverted organic solar cell (ITO cathode / cathode interface layer / active layer / anode-machine interface layer / anode)

[0055] Pre-cut the ITO conductive glass with a square resistance of 20 ohms / cm2 into 15mm×15mm square pieces. Use acetone, special detergent for micron-sized semiconductors, deionized water, and isopropanol to clean ultrasonically in sequence, blow nitrogen whistle, and place in a constant temperature oven for later use. Take a chloroform solution of conjugated polymer PFN‐V and 1,8‐octanedithiol (mass ratio 1:0.77), and spin-coat it on ITO with a thickness of about 8 nm. The films were then irradiated under UV light for 5 seconds to complete the cross-linking. Then spin-coat the active layer material PTB7‐Th:PC 71 BM (mass ratio 1:1.5), with a thickness of 100 nm, and finally vapor-deposited MoO3 and Al electrodes. All preparations were...

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Abstract

The invention relates to the preparation of a cross-linked electrode modification material by adopting ethylenic bond-mercapto click chemistry method and its application in organic electronic devices. The cross-linked electrode modification material of the present invention is produced by a click chemical reaction of a conjugated polymer containing an ethylenic bond in a side chain and a dimercapto small molecule additive under the condition of ultraviolet light or heating. The prepared cross-linked electrode modification material has good resistance to solvent elution and is suitable for making complex multilayer organic electronic devices. The cross-linked electrode modification material can improve the work function of the metal / metal oxide and enhance the electron extraction ability of the metal / metal oxide electrode. The cross-linked electrode modification material prepared by the ethylenic bond-mercapto click chemistry method of the present invention can be applied in organic photoelectric devices to improve device performance.

Description

technical field [0001] The invention relates to the field of macromolecule photoelectric materials and devices, in particular to the preparation of cross-linked electrode modification materials by an olefin-mercapto click chemistry method and its application in organic electronic devices. Background technique [0002] Since the 20th century, organic optoelectronics have developed rapidly. Organic electroluminescent diodes and organic solar cells have received extensive attention from both academia and industry. [0003] Inorganic solar cells represented by inorganic silicon have been relatively maturely applied in the market, but there are many problems in the production process, such as high energy consumption, high cost of raw materials, and serious pollution. Organic solar cell devices have broad application prospects because of their flexible material design, large-area, low-cost solution processing, semi-transparent, flexible and other outstanding advantages. [0004]...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/02H01L51/00H01L51/52H10K99/00
CPCC08G61/02C08G2261/91C08G2261/411C08G2261/414C08G2261/3142C08G2261/18H10K85/10H10K50/82Y02E10/549
Inventor 黄飞林凯王晶胡志诚曹镛
Owner 中山市东石材料科技有限公司
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