Monocarbazole/dicarbazole hole transport material as well as preparation method and application thereof

A hole transport material and biscarbazole technology, applied in the field of single/bicarbazole hole transport materials and their preparation, can solve the problems of lack of hole transport materials, complex synthesis routes, harsh reaction conditions, etc., and achieve high application Value, low cost, effect of improving molecular packing and hole transport capability

Active Publication Date: 2020-11-10
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the hole transport materials used in PSCs are mainly triphenylamine structures, the most used is spiro-OMeTAD, and there is a lack of more alternative hole transport materials.
Moreover, the synthesis cost of spiro-OMeTAD is expensive, the synthesis route is complicated, and the reaction conditions are harsh. Therefore, it is necessary to develop a high-performance hole transport material. At the same time, reducing the synthesis cost, simplifying the synthesis route, and improving the conversion efficiency have become problems that need to be solved urgently.

Method used

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  • Monocarbazole/dicarbazole hole transport material as well as preparation method and application thereof
  • Monocarbazole/dicarbazole hole transport material as well as preparation method and application thereof
  • Monocarbazole/dicarbazole hole transport material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Synthesis of Example 1 Hole Transport Material A1

[0069] 1. Synthesis of compound 1

[0070]

[0071] The reaction device was treated with anhydrous and protected by argon. Add DMF (12.3mL, 160.00mmol, 20.00eq) into a 25mL two-necked flask, stir in an ice-water bath for 20min, then slowly add POCl 3 (7.5mL, 80.00mmol, 10.00eq), with dried CH 2 Cl 2 Dissolve N-ethylcarbazole (1.5621g, 8.00mmol, 1.00eq) in (6.0mL), slowly drop into the two-necked flask at room temperature, stir for 10min, heat at 90°C for reaction, stop the reaction after 21h, and saturated saline / acetic acid Ethyl extraction was performed, the organic layer was dried over anhydrous magnesium sulfate, and column chromatography (ethyl acetate: petroleum ether = 1:3, v / v) yielded 1.2402 g of the target product with a yield of 61.7%. 1 H NMR (400MHz, CDCl 3 ): δ(TMS,ppm)=10.14(s,2H),8.68(s,2H),8.10(d,J=8Hz,2H),7.56(d,J=8Hz,2H),4.47(q,J =8Hz, 2H), 1.52(t, J=8Hz, 3H), such as figure 1 As shown, com...

Embodiment 2

[0084] Synthesis of Example 2 Hole Transport Material A4

[0085] 1. Synthesis of Compound 5

[0086]

[0087] The reaction device was treated with anhydrous and protected by argon. Add compound 2 (0.1527g, 0.50mmol, 1.00eq.), N-iodosuccinimide (0.1237g, 0.55mmol, 1.10eq.) and N,N-dimethylformamide into a 25mL two-necked flask Amide (4.0mL), react at room temperature for 23h, extract with saturated brine / ethyl acetate, dry the organic layer with anhydrous magnesium sulfate, and perform column chromatography (ethyl acetate:petroleum ether=1:50, v / v) to obtain the target product 0.2100 g, yield 97.4%. 1 H NMR (400MHz, CDCl 3 ): δ(TMS,ppm)=7.30(d,J=8Hz,2H),6.93(d,J=8Hz,4H),6.72(d,J=8Hz,4H),6.58(d,J=8Hz, 2H),3.68(s,6H), such as Image 6 As shown, compound 5 was obtained.

[0088] 2. Synthesis of Compound 6

[0089]

[0090] The reaction device was treated with anhydrous and protected by argon. Add compound 5 (0.1941g, 0.45mmol, 1.00eq.), trimethylsilylacetylene (0.08...

Embodiment 3

[0097] Example 3 Optical and electrical performance characterization of hole transport materials A1 and A4 and their application in the preparation of perovskite solar cells

[0098] The above-mentioned synthesized hole-transport materials A1 and A4 and the existing hole-transport material spiro-OMeTAD were tested for photophysical properties (ultraviolet, fluorescence), electrochemical properties, etc. The specific test methods and results are as follows:

[0099] (1) Ultraviolet-visible absorption spectrum: the instrument model is Shimadzu UV-3600, and the sample is scanned at a wavelength of 200-800nm, and the results are as follows Figure 10 As shown, it shows that A1 and A4 mainly absorb around 300-400nm, effectively avoiding the absorption in the visible light region, and have little influence on the light absorption of the perovskite layer. The spectral onset absorption wavelength can be obtained by the formula △E g =hc / λ onset , to calculate the band gap width.

[...

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Abstract

The invention discloses a monocarbazole/dicarbazole hole transport material as well as a preparation method and application thereof. The chemical structural general formula of the monocarbazole/dicarbazole hole transport material is shown as a formula I. Herein, N-ethyl carbazole or N,N'-dicarbazole is used as a core, alkoxy or alkylthio substituted triphenylamine is used as a side group, and an olefinic bond or an acetylene bond is introduced between the core and the side group to increase a conjugated system and regulate and control the molecular accumulation capability and the hole transport capability of the conjugated system. A photophysical property (ultraviolet and fluorescence) test, an electrochemical performance test and a photovoltaic device performance test show that the chargetransport material has good performance and has the characteristics of simplicity in synthesis, low raw material cost, high performance efficiency and the like; therefore, the material can be appliedto photoelectric devices such as organic photosensitive drums, organic light-emitting diodes and solar cells as a hole transport material, and has a wide application prospect.

Description

technical field [0001] The present invention relates to the technical field of optoelectronic materials, more specifically, to a single / biscarbazole hole transport material and its preparation method and application. Background technique [0002] With the continuous development of science and technology, optoelectronic technology is becoming more and more closely related to people's life, and emerging technologies such as organic photoconductor drum (OPC), organic light-emitting diode (OLED) and solar cells are becoming more and more important. OPC is an important information functional material, which can be widely used in electrostatic copying, holographic photography, laser printing, etc. One of the key materials of OPC is the charge transport material. At the same time, the charge transport material provides an effective channel for the transport of carriers in the OLED. It is an indispensable part of the OLED device and is also the research focus of electronic materials...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86G03G5/06H01L51/42H01L51/54
CPCC07D209/86G03G5/0629H10K85/631H10K85/6572H10K30/10H10K50/15Y02E10/549
Inventor 邵光高伟杰余恵娟
Owner SUN YAT SEN UNIV
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