Block copolymers based on naphthalene diimide and indacene cyanindanone based on the main chain structure and their applications in organic photovoltaic devices

A technology for introducing and saving cyanoindanone and naphthalene diimide, which is applied in the field of polymer photoelectric materials, can solve the problems of uncontrollable phase separation and low absorption coefficient of active layer films, and achieves high performance and high absorption coefficient. Effect

Active Publication Date: 2020-06-05
东莞伏安光电科技有限公司
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  • Abstract
  • Description
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Problems solved by technology

The main reason is that the absorption coefficient of the existing receptor is not high, and the phase separation of the active layer film is uncontrollable.

Method used

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  • Block copolymers based on naphthalene diimide and indacene cyanindanone based on the main chain structure and their applications in organic photovoltaic devices
  • Block copolymers based on naphthalene diimide and indacene cyanindanone based on the main chain structure and their applications in organic photovoltaic devices
  • Block copolymers based on naphthalene diimide and indacene cyanindanone based on the main chain structure and their applications in organic photovoltaic devices

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Synthetic route see Figure 7 ~ Figure 8 .

[0041] (1) Monomers M1, M2, and M3 were synthesized according to the method disclosed in the literature [Journal of medicinal chemistry, 2013, 56(7): 2959-2974.].

[0042] (2) Monomer M4 was synthesized according to the method disclosed in the literature [Advanced Functional Materials, 2015, 25(23): 3514-3523.].

[0043] (3) Monomers M5, M6, and M7 were synthesized according to the method disclosed in the literature [Journal of the American Chemical Society, 2011, 133(5): 1405-1418.].

[0044] (4) Synthesis of polymers P1, P2, P3:

[0045]Add monomer M1 (0.4mmol) and monomer M5 (0.5mmol) into a 25mL two-necked flask, pass through nitrogen protection, and add 8mL of toluene. Add 5mg Pd(PPh 3 ) 4 After reacting at 95°C for 1 h, monomer M4 (0.1 mmol) was added, and after continuing the reaction for 12 h, the polymer was precipitated with methanol and washed three times. A dark polymer P1 was obtained with a yield of 80.7%....

Embodiment 2

[0053] The conjugated polymers P1, P2, and P3 synthesized in Example 1 are used as electron acceptors in organic photovoltaic devices (ITO cathode / cathode interface layer / active layer / anode-machine interface layer / anode)

[0054] 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. Spin-coat a layer of 5nm thick PFN-Br on ITO, then spin-coat active layer materials PBDB-T / P1, PBDB-T / P2, PBDB-T / P3 with a thickness of 110nm, and finally evaporate MoO 3 and Al electrodes. All preparations were carried out in a glove box under a nitrogen atmosphere. The current-voltage curves of the fabricated flip-chip devices are as follows: Figure 4 The relevant data are listed in Table 1. It can be seen that the main chain structur...

Embodiment 3

[0056] Using the conjugated polymers P1, P2, and P3 synthesized in Example 1 (the AB components are the same in the structure) as electron acceptors in organic photovoltaic devices (ITO anode / anode interface layer / active layer / cathode interface layer / cathode) middle application

[0057] 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. Spin-coat a layer of PEDOT:PSS with a thickness of 20nm on the ITO, and then spin-coat active layer materials PBDB-T / P1, PBDB-T / P2, and PBDB-T / P3 with a thickness of 100nm. Then spin-coat a layer of PFN-Br with a thickness of 5nm, and finally evaporate Al electrodes. All preparations were carried out in a glove box under a nitrogen atmosphere. The current-voltage curves of the prep...

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Abstract

The invention belongs to the technical field of macromolecule photoelectric materials, and discloses a block copolymer based on naphthalene diimide and indacene cyanindanone based on the main chain structure and its application in organic photovoltaic devices. The copolymer of the present invention has the following structure: wherein, n is a positive integer less than or equal to 1 million, 0<X≤1, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 The same or different ones are alkyl chains; A and B are conjugated unit structures, the same or different ones are thiophene, furan, bithiophene, bifuran, thiophene bifuran, thiophene, and furan and derivatives of all the above structures C is an aromatic ring and is at least one of benzene, thiophene, furan, selenophene, pyrrole, thiazole, imidazole, pyridine, pyrazine, pyrimidine, and pyridazine. The polymer of the invention not only has relatively regular stacking, but also has a high absorption coefficient, and can be used as a high-efficiency electron acceptor in high-efficiency organic photovoltaic devices to effectively improve the performance of the devices.

Description

technical field [0001] The invention belongs to the technical field of polymer optoelectronic materials, in particular to a block copolymer based on naphthalene diimide and indacene cyanindanone based on the main chain structure and its application in organic photovoltaic devices. Background technique [0002] With the increasing global demand for energy, the depletion of traditional energy sources such as oil and coal, and the need to protect the earth's ecological environment, more and more scientists around the world are focusing their research on inexhaustible hydrogen, solar energy, etc. Inexhaustible renewable clean energy. [0003] Mature photovoltaic devices based on inorganic materials such as inorganic silicon, gallium arsenide, and indium phosphide have dominated the market. However, due to their high requirements for material purity, high energy consumption and pollution will occur during processing. And its price is very expensive, so its large-scale applicatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/42H01L51/46
CPCC08G61/124C08G61/125C08G61/126C08G2261/414C08G2261/91C08G2261/51C08G2261/122C08G2261/1412C08G2261/3222C08G2261/3243C08G2261/3241C08G2261/143C08G2261/18H10K85/151H10K30/00Y02E10/549
Inventor 黄飞胡志诚应磊曹镛
Owner 东莞伏安光电科技有限公司
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