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Structure, synthesis and application of spirobifluorene hole-transport materials (2,4-spiro-OMeTAD)

A hole transport material, spirobifluorene technology, applied in the direction of luminescent materials, preparation of organic compounds, preparation of aminohydroxy compounds, etc., can solve the problems of difficult purification, harsh synthesis conditions, and high synthesis costs, and achieves good solubility and cost. Low, good stability

Active Publication Date: 2017-06-06
NANJING UNIV OF INFORMATION SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The currently used hole-transporting material is Spiro-OMeTAD. Due to its high synthesis cost, harsh synthesis conditions, and difficult purification, researchers are trying to find other suitable hole-transporting materials.

Method used

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  • Structure, synthesis and application of spirobifluorene hole-transport materials (2,4-spiro-OMeTAD)
  • Structure, synthesis and application of spirobifluorene hole-transport materials (2,4-spiro-OMeTAD)
  • Structure, synthesis and application of spirobifluorene hole-transport materials (2,4-spiro-OMeTAD)

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Example 1: Preparation and performance characterization of spirobifluorene hole transport material 2,4-spiro-OMeTAD

[0032] 2,4-dimethoxyaniline (1.00g, 6.54mmol), bromobenzene (0.95g, 7.19mmol), sodium tert-butoxide (0.94g, 9.80mmol), tri-tert-butylphosphine (0.021g, 0.10mmol ), tris(dibenzylideneacetone)dipalladium (0.06g, 0.07mmol), and 15ml of anhydrous toluene were heated to 110°C under the protection of argon, and the temperature was maintained and stirred for 12 hours. After cooling to room temperature, extract with ethyl acetate and brine (saturated sodium chloride solution), the organic phase was dried and concentrated to obtain a crude product, and the crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:100 ) to obtain compound 1. The hydrogen spectrum data of compound 1 is: 1 H NMR (CDCl 3 400Hz) δ=3.84(s,3H),3.87(s,3H),6.49(dd,1H,J1=4Hz,J2=4Hz),6.58(d,1H,J=4Hz),6.89(m,1H) ,7.04(m,2H),7.27(m,3H).

[0033] Compound 1 (1....

Embodiment 2

[0040] Example 2: Preparation and performance characterization of solar cells based on the TDT-OMeTPA hole transport material of the present invention

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Abstract

The invention discloses a structure, synthesis and application of spirobifluorene hole-transport materials (2,4-spiro-OMeTAD). The hole-transport materials are spirobifluorene hole-transport materials; a preparation method of the spirobifluorene hole-transport materials comprises the steps of heating a mixed system, which is formed by a compound 1, spirobifluorene, sodium tert-butoxide, tri-tert-butylphosphine, tris(dibenzylideneacetone) dipalladium and anhydrous toluene, up to 105-115 DEG C under the protection of argon, maintaining the temperature and reacting for 10-14h; cooling, then extracting to obtain an organic phase by using ethyl acetate, drying and concentrating the obtained organic phase, and then carrying out silica gel column chromatography to obtain a target product 2,4-spiro-OMeTAD. The hole-transport material 2,4-spiro-OMeTAD is high in hole mobility, has an HOMO energy level matched with the valence band of a perovskite material, is good in stability and dissolving capacity, and high in molar extinction coefficient; a perovskite solar battery prepared from the 2,4-spiro-OMeTAD is high in photoelectric converting efficiency; due to the flexible change of a methyl position, the structural modification can be conveniently carried out at the later period, and the spectrum absorption from an ultraviolet light area to a near infrared light area is easily realized; the commercialization cost is low.

Description

technical field [0001] The invention belongs to the field of optoelectronics and relates to novel photoelectric transmission materials, in particular to the structure, synthesis and application of a three-dimensional spirobifluorene hole transport material in perovskite solar cells. Background technique [0002] In recent years, due to the increasing shortage of fossil energy and the serious pollution caused by its use to the surrounding environment, finding and utilizing clean renewable energy has become one of the major tasks for the sustainable development of human civilization. Thin-film, high conversion efficiency, abundant raw materials and non-toxic third-generation solar cells are increasingly showing attractive development prospects. Among them, since organic-inorganic hybrid halogen perovskite materials were first applied to photovoltaic devices in 2009, the photoelectric conversion efficiency of perovskite cells has reached close to 20% in 2014, surpassing organic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/92C07C213/02C09K11/06H01L51/46
CPCC09K11/06C07C213/02C07C217/92C09K2211/1007C09K2211/1011C09K2211/1014H10K85/633H10K30/00Y02E10/549
Inventor 张明道赵丹霞曹晖焦岩
Owner NANJING UNIV OF INFORMATION SCI & TECH
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