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Spiro[fluorene-9,9'-oxanthene] derivatives based on polythiafulvalene substitution and their preparation and application

A technology of thiafulvalene and dithiafulvalene, which is applied in semiconductor/solid-state device manufacturing, organic chemistry, electrical solid-state devices, etc., can solve the problems of high hole mobility and low solubility, and achieve good film formation , low-cost effect

Active Publication Date: 2021-03-19
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These compounds have low solubility and still require the use of additives to achieve high hole mobility

Method used

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  • Spiro[fluorene-9,9'-oxanthene] derivatives based on polythiafulvalene substitution and their preparation and application
  • Spiro[fluorene-9,9'-oxanthene] derivatives based on polythiafulvalene substitution and their preparation and application
  • Spiro[fluorene-9,9'-oxanthene] derivatives based on polythiafulvalene substitution and their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048]

[0049] At room temperature, dissolve 2.0g (3.1mmol) of 2,2',7,7'-tetrabromospiro[fluorene-9,9'-oxanthene] in 70mL of dry tetrahydrofuran; after the solid is completely dissolved, cool down to -78°C, N 2 Slowly add 24.6g (46.4mmol) of tert-butyl lithium dropwise under protection. After the dropwise addition, keep stirring at low temperature for 7h; slowly add 4.5g (62.0mmol) of dry N,N-dimethylformamide dropwise, and continue to The reaction was stirred for 2h. After the reaction was completed, 30 mL of 2 mol / L dilute hydrochloric acid was added to the reaction solution to quench the reaction. After the reaction solution was naturally warmed to room temperature, the organic phase was extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. Using n-hexane and dichloromethane at a volume ratio of 1:1 as the eluent, the crude product was purified by column chromatography to obtain the ligh...

Embodiment 2

[0058]

[0059] At room temperature, dissolve 3.0g (4.65mmol) of 2,3',6',7-tetrabromospiro[fluorene-9,9'-oxanthene] in 110mL of dry tetrahydrofuran; after complete dissolution, cool down to - 78°C, N 2 Slowly add 36.9g (69.6mmol) of tert-butyl lithium dropwise under protection. After the dropwise addition, keep stirring at low temperature for 7h; slowly add 6.75g (93.0mmol) of dry N,N-dimethylformamide dropwise, and continue to The reaction was stirred for 2h. After the reaction was completed, 30 mL of 2 mol / L dilute hydrochloric acid was added to the reaction solution to quench the reaction. After the reaction solution was naturally warmed to room temperature, the organic phase was extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. Using n-hexane and dichloromethane at a volume ratio of 1:1 as the eluent, the crude product was purified by column chromatography to obtain the light yellow ...

Embodiment 3

[0068] In this embodiment, the single-carrier devices of SFX-DTF1 and SFX-DTF2 described in Example 1 and Example 2 are produced, and the single-carrier devices are tested by using the method of space charge limiting current, so as to calculate and obtain SFX respectively - Hole mobilities of DTF1 and SFX-DTF2, and compared with that of the commercial hole transport material Spiro-OMeTAD.

[0069] The specific single-carrier device structure is: ITO / PEDOT:PSS (40 nm) / SFX-DTF1 or SFX-DTF2 (55 nm) / MoO 3 (5 nm) / Al (80 nm).

[0070] The hole transport material SFX-DTF1 or SFX-DTF2 was dissolved in chlorobenzene to obtain a hole transport layer material solution with a concentration of 10 mg / ml. Spin-coat PEDOT:PSS on the pre-cleaned and ozone-treated ITO surface, dry at 120°C for 15 minutes, then spin-coat a certain thickness of hole transport layer material, and then vapor-deposit the upper electrode MoO on the surface of the hole transport layer. 3 / Ag, to obtain a si...

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Abstract

The present invention discloses a snail [芴 ‑ 9, 9'‑ oxygen hydrocephaly] derivative represented by a structural generally expressed structure.Can reach 1.51 × 10 ‑4 CM 2 V ‑1 S ‑1 For non -doped perovskite solar cells, it can obtain more than 10%photoelectric conversion efficiency.

Description

technical field [0001] The invention belongs to the technical field of new organic semiconductor materials, and relates to a polythiafulvalene derivative, in particular to a spiro[fluorene-9,9'-oxa with a dithiafulvalene derivative as a peripheral substituent. Anthracene] derivatives. [0002] technical background [0003] Organic semiconductor materials have abundant sources of raw materials, are light in weight, easy to process, and can be formed into large-area films by solution methods. They are widely used in organic electroluminescent diodes, solar cells, and organic thin-film field-effect transistors. In particular, organic-inorganic halide perovskite solar cells, which have developed rapidly in recent years, use halide perovskite as the solar light harvesting layer, and select organic hole transport materials to prepare the transport layer, and have obtained a photoelectric conversion efficiency of more than 22%. . Among them, hole transport materials play an import...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14H01L51/46H01L51/42
CPCC07D409/14H10K85/655H10K85/6574H10K30/151Y02E10/549
Inventor 郭鹍鹏王忠强李洁吴敏张如芹梁效中吴月珍张芳
Owner TAIYUAN UNIV OF TECH
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