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Preparation and application of arylamine derivatives substituted phenol or alkoxybenzene small molecule hole transport materials

A technology of hole transport material and hole transport layer, which is applied in the preparation of organic compounds, preparation of amino hydroxyl compounds, semiconductor/solid-state device manufacturing, etc., can solve the problem of unstudied hole transport performance and unreported arylamine trisubstituted phenol Derivatives and other issues, to achieve good hole transport performance, good electron blocking performance, performance improvement effect

Inactive Publication Date: 2018-09-14
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the literature Dyes and Pigments, 2015, 113, 640-648 and Chemical Communications, 2007, 1, 70-72, they reported trisubstituted alkoxybenzene derivatives of arylamines, studied their electrochemical properties and aggregation-induced luminescent properties and potential Related applications; more importantly, none of them reported the derivatives of arylamine trisubstituted phenols, nor did they study their hole transport properties

Method used

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  • Preparation and application of arylamine derivatives substituted phenol or alkoxybenzene small molecule hole transport materials
  • Preparation and application of arylamine derivatives substituted phenol or alkoxybenzene small molecule hole transport materials
  • Preparation and application of arylamine derivatives substituted phenol or alkoxybenzene small molecule hole transport materials

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Experimental program
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Effect test

Embodiment 1

[0038] The tribromophenol and bromo-n-octane are dissolved in toluene, then sodium hydroxide is added, and the reaction is carried out at 60°C for 5 hours. The reaction product is separated and purified to obtain tribromo-n-octyloxybenzene with a yield of 90%. Dissolve tribromo-octoxybenzene (0.5g) and N-phenylcarbazole-3-boronic acid (2.17g, 7.5mmol) in 100ml of toluene solution, then add 25mL ethanol and 20mL 2M sodium carbonate aqueous solution, nitrogen After venting for 20 minutes, add tetrakistriphenylphosphonium palladium (23mg, 0.02mmol), under nitrogen atmosphere, heat up to 90°C for 12 hours, cool to room temperature, remove the solvent under reduced pressure, separate with silica gel column, and use petroleum ether / two Methyl chloride = 1:1 (v / v) was used as the eluent to obtain the crude product, which was spin-dried to concentrate the solvent, and then washed with petroleum ether three times to obtain a white product with a yield of 30%. 1 H-NMR(DMSO-d 6 ,400MHz)δ8....

Embodiment 2

[0040] Dissolve tribromophenol (0.5g) and N-phenylcarbazole-3-boronic acid (2.17g, 7.5mmol) in 100ml of toluene solution, then add 25ml of ethanol and 20ml of 2M sodium carbonate aqueous solution, and vent with nitrogen for 20 minutes , Add palladium tetrakistriphenylphosphorus (23mg, 0.02mmol), under nitrogen atmosphere, heat up to 90℃ and react for 12h, then cool to room temperature, remove the solvent under reduced pressure, separate with silica gel column, with petroleum ether / dichloromethane=1 :1(v / v) is used as the eluent to obtain the crude product, and then washed with petroleum ether 3 times to obtain a pure white product with a yield of 75%. 1 H-NMR(DMSO-d 6 , 400MHz) δ8.72-8.67 (s, 1H); 8.59-8.54 (s, 2H); 8.42-8.31 (m, 4H); 7.90-7.63 (m, 17H); 7.60-7.26 (m, 15H). The solubility of the product in toluene and dimethyl sulfoxide is greater than 20mg / mL, and its ultraviolet absorption and fluorescence intensity curve in toluene solution are as follows figure 2 Shown.

Embodiment 3

[0042] Dissolve tribromophenol and bromo-n-ethane in tetrahydrofuran, then add sodium carbonate aqueous solution and react for 5h at 70°C. The reaction product is separated and purified to obtain tribromoethoxybenzene with a yield of 90%. Dissolve tribromoethoxybenzene (0.5g, 1.5mmol) and 4-(9-carbazolyl)phenylboronic acid (2.60g, 9mmol) in 100ml of dioxane solution, then add 20mL of 2M sodium carbonate aqueous solution After venting with nitrogen for 20 minutes, add tetrakistriphenylphosphonium palladium (23mg, 0.02mmol). Under nitrogen atmosphere, heat up to 110°C and react for 12h, then cool to room temperature, remove the solvent under reduced pressure, and separate with silica gel column. / Dichloromethane=1:1 (v / v) as the eluent to obtain the crude product, and then wash with petroleum ether 3 times to obtain the pure white product, the yield is 75%, and the solubility of the product in toluene is greater than 20mg / mL.

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses a small molecule hole transport material substituted by aromatic amine derivatives for phenol or alkoxybenzene, as well as its preparation and application. The hole transport material has a general structural formula represented by formula (1) or (2). The preparation method is as follows: dissolving tribromophenol or tribromoalkoxybenzene and aromatic amine boric acid derivatives in an organic solvent, then adding an aqueous alkali solution, adding a palladium catalyst under nitrogen, and reacting at 30-110°C for 0.5-48 hours , The reaction product was separated and purified to obtain the product. The present invention introduces electron-donating arylamine derivatives at the ortho and para positions of phenol or alkoxybenzene through the Suzuki reaction one-step method, and the obtained products have good hole transport performance and electron blocking performance, especially aromatic amine derivatives. The trisubstituted phenol is easy to be doped with lead metal cations, and has good hole transport performance without the need for additional dopants, and can be used in perovskite solar cells and other fields.

Description

Technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and specifically relates to the preparation and application of an aromatic amine derivative substituted phenol or alkoxybenzene small molecule hole transport material. Background technique [0002] In 1986, Dr. Qingyun Deng reported an organic double-layer heterojunction photovoltaic device with an energy conversion efficiency of about 1%. After decades of development, photovoltaic materials and device structures have made great progress. The device efficiency of organic polymer heterojunction solar cells exceeds 10%. What is more striking is the efficiency of the new perovskite solar cell exceeds 20%, and its structure is shown as figure 1 As shown, by introducing transport injection materials with different functions on both sides of the active layer, the transport efficiency after separation of electrons and holes is improved, thereby improving the overall performance of the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07C215/74C07C213/02H01L51/54H01L51/46
CPCC07C213/02C07C215/74C07D209/86H10K85/631H10K85/6572H10K30/00H10K50/157H10K50/15Y02E10/549H10K85/50
Inventor 李远邱学青薛雨源
Owner SOUTH CHINA UNIV OF TECH
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