Benzotriazole boron nitrogen derivative small molecular material and application thereof in organic electronic device

A technology for benzotriazole boron nitrogen and organic electronic devices, which is applied to small molecule materials of benzotriazole boron nitrogen derivatives and its application in organic electronic devices, can solve the problem of low HOMO/LUMO energy level and realize the Market barriers, affecting device efficiency and other issues, to achieve the effect of improving battery efficiency, wide absorption range, and long device life

A technology for benzotriazole boron nitrogen and organic electronic devices, which is applied to small molecule materials of benzotriazole boron nitrogen derivatives and its application in organic electronic devices, can solve the problem of low HOMO/LUMO energy level and realize the Market barriers, affecting device efficiency and other issues, to achieve the effect of improving battery efficiency, wide absorption range, and long device life

CN113549097APending Publication Date: 2021-10-26HUAIYIN INSTITUTE OF TECHNOLOGY
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  • Benzotriazole boron nitrogen derivative small molecular material and application thereof in organic electronic device
  • Benzotriazole boron nitrogen derivative small molecular material and application thereof in organic electronic device
  • Benzotriazole boron nitrogen derivative small molecular material and application thereof in organic electronic device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of compound 1

[0029]

[0030] Add 1-1 (6.44g, 6mmol), 1-2 (3.86g, 20mmol) and 5mL pyridine into a 500mL two-necked flask, then pump argon three times, add 250mL chloroform under the protection of argon, and react at 65°C 24 hours. Cool to room temperature, extract three times with dichloromethane, combine the organic phases, dry filter and spin dry with silica gel, separate and purify by column chromatography (n-hexane: dichloromethane = 3:1) to obtain 3.84 g of purple powder, yield 45% . MS(EI)m / z:[M]+:1423.56.

Embodiment 2

[0031] Embodiment 2: the synthesis of compound 2

[0032]

[0033] Add 1-1 (5.37g, 5mmol), 1-3 (3.91g, 16mmol) and 5mL pyridine into a 500mL two-necked flask, then pump argon three times, add 300mL chloroform under the protection of argon, and react at 65°C for 24 hours . Cool to room temperature, extract three times with dichloromethane, combine the organic phases, dry filter and add silica gel to spin dry, separate and purify by column chromatography (n-hexane:dichloromethane=3:1) to obtain 2.98g of purple powder, yield 39% . MS(EI)m / z:[M]+:1526.62.

Embodiment 3

[0034] Embodiment 3: the synthesis of compound 3

[0035]

[0036] Add 1-1 (6.44g, 6mmol), 1-4 (4.57g, 20mmol) and 5mL pyridine into a 500mL two-neck flask, then pump argon three times, add 300mL chloroform under the protection of argon, and react at 65°C for 24 hours . Cool to room temperature, extract three times with dichloromethane, combine the organic phases, dry filter and add silica gel to spin dry, separate and purify by column chromatography (n-hexane:dichloromethane=3:1) to obtain 3.32 g of purple powder, yield 37% . MS(EI)m / z:[M]+:1493.56.

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Abstract

The invention discloses a benzotriazole boron nitrogen derivative small molecular material and application thereof in an organic electronic device. The compound is an n-type non-fullerene acceptor material taking benzotriazole with an alkyl chain as a central core. An organic electronic device comprises at least one compound as described above. The invention relates to a benzotriazole boron nitrogen derivative, which has infrared absorption with long absorption wavelength, and the absorption spectrum of the benzotriazole boron nitrogen derivative has a wide absorption range and high photoelectric conversion efficiency. An organic solar cell element prepared from the benzotriazole boron nitrogen derivative has high photoelectric conversion efficiency and long device service life; boron and nitrogen have opposite resonance effects, the corresponding boron-nitrogen fused ring compound can improve the triplet state energy level of molecules, but does not affect the accumulation and film formation of the molecules, the recombination loss is reduced, and the battery efficiency is effectively improved.

Description

technical field [0001] The invention relates to the technical field of organic solar energy, in particular to a benzotriazole boron nitrogen derivative small molecule material and its application in organic electronic devices. Background technique [0002] With the increasingly serious energy problems, replacing fossil fuels with sustainable energy in power production has become an effective way to solve energy problems. Solar energy has great development prospects due to its inexhaustible and inexhaustible advantages. The installed capacity of silicon solar cells is rapidly increasing worldwide, but it is also possible that new generation solar cell technology will mature as a sustainable technology in the near future and also contribute to this transition. Organic solar cells (Organic Solar Cells, OPV) have been intensively studied for many years and have begun to be applied in the market due to their translucency, flexibility, rollability, light weight, portability, and c...

Claims

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Application Information

Patent Timeline
26 Oct 2021
Publication
CN113549097A
IPC
C07F5/02; H01L51/46
CPC
C07F5/02; C07F5/025; H10K85/656; H10K85/626; H10K85/6576; H10K85/657; Y02E10/549
Inventors
胡光; 王子鸣