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Structure, synthesis and application of a spirobifluorene-based hole-transporting material

A technology of hole transport materials and spirobifluorene, which is applied in the direction of luminescent materials, preparation of organic compounds, preparation of amino hydroxyl compounds, etc., can solve the problems of high synthesis cost, harsh synthesis conditions, and difficult purification, and achieve low cost and stability Good performance and good solubility

Active Publication Date: 2019-04-23
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 a spirobifluorene-based hole-transporting material
  • Structure, synthesis and application of a spirobifluorene-based hole-transporting material
  • Structure, synthesis and application of a spirobifluorene-based hole-transporting material

Examples

Experimental program
Comparison scheme
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 HNMR (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 (1.0...

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 the structure, synthesis and application of a spirobifluorene hole transport material. The hole transport material is a spirobifluorene hole transport material. The preparation steps are as follows: compound 1, spirobifluorene, t- The mixed system of sodium butoxide, tri-tert-butylphosphine, tris(dibenzylideneacetone) dipalladium and anhydrous toluene is heated to 105-115°C under the protection of argon, and the temperature is maintained for 10-14 hours; after cooling The organic phase was extracted with ethyl acetate, and the organic phase was dried and concentrated, followed by silica gel column chromatography to obtain the target product 2,4‑spiro‑OMeTAD. The hole transport material 2,4-spiro-OMeTAD of the present invention has high hole mobility, the HOMO energy level matches the valence band of perovskite, good stability, good solubility, and high molar extinction coefficient, and the perovskite made of it The photoelectric conversion efficiency of the mineral solar cell is high; the flexible change of its methyl position facilitates structural modification in the later stage, and it is easy to realize spectral absorption in the ultraviolet to near-infrared light region; and 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 Patents(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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