A Method for Enhancing Molecular Planarity of Non-Screw Organic Small Molecule Hole Transport Materials

A hole transport material and small molecule technology, which is applied in the field of molecular planarity enhancement of non-spiro-type organic small molecule hole transport materials, can solve the problems of inability to achieve conjugation, increased manufacturing costs, high synthesis costs, etc. Hole mobility, enhanced molecular planarity, enhanced effect of π-π stacking

Active Publication Date: 2022-05-10
HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Currently, the most commonly used small organic molecule hole transport material is 2,2,7,7-tetrakis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobifluorene (spiro- OMeTAD), which has many synthetic steps, harsh conditions and complicated purification process, resulting in high synthetic cost
In addition, in order to ensure the hole mobility, chemical additives need to be used, which increases the manufacturing cost and reduces the environmental stability of the device, which is not conducive to the commercialization of perovskite solar cells.
At present, many studies use triphenylamine as the terminal and the non-helical molecule with the non-helical group as the core as a substitute for spiro-OMeTAD. yoke, most alternatives cannot combine good performance and lower cost

Method used

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  • A Method for Enhancing Molecular Planarity of Non-Screw Organic Small Molecule Hole Transport Materials
  • A Method for Enhancing Molecular Planarity of Non-Screw Organic Small Molecule Hole Transport Materials
  • A Method for Enhancing Molecular Planarity of Non-Screw Organic Small Molecule Hole Transport Materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Synthesis of compound M0:

[0040]

[0041] Specific steps are as follows:

[0042] In a 50mL round-bottomed flask, an aqueous solution of compound 1 (458mg, 1mmol), 4-boronate-4', 4'-dimethoxytriphenylamine (1.08g, 2.5mmol), potassium carbonate ( 4M, 4mL), Pd(PPh 3 ) 4 (57 mg, 0.05 mmol), anhydrous DMF (20 mL) and absolute ethanol (4 mL). The reaction solution was stirred at 120° C. for 24 hours under nitrogen protection. After the reaction was cooled to room temperature, the reaction mixture was extracted with ethyl acetate and washed with saturated brine. The organic phase was dried with anhydrous magnesium sulfate and concentrated by rotary evaporation, and the obtained crude product was separated by column chromatography, using petroleum ether / dichloromethane (v / v=5 / 1) as eluent, and reacted to obtain 589 mg of a purple solid Product, yield 65%. 1H NMR (300MHz, CDCl 3 )δ8.10-8.09(d,2H), 7.84(s,2H), 7.51-7.48(d,4H), 7.28-7.27(d,2H), 7.10-7.06(m,8H), 6....

Embodiment 2

[0050] Compound M2 and compound M0 synthesized in Example 1 were used to prepare single-hole device FTO / PEDOT:PSS / HTM / Au respectively, and obtained by space-limited current method as follows: figure 2 J shown 1 / 2 – V-curve (SCLC) to estimate hole mobility. As a result, the hole mobility of M2 was calculated to be 1.33×10 -6 cm 2 V -1 the s -1 , the hole mobility of M0 is 8.92×10 -7 cm 2 V -1 the s -1 . It can be seen that the void mobility of compound M2 is significantly higher than that of compound M0.

Embodiment 3

[0052] The compound M2 synthesized in Example 1 and its compound M0 are used as undoped hole transport materials in organic-inorganic perovskite solar cells, and their structure is: FTO / ETM / m-TiO 2 / MAPB 3 / HTM / Au, such as image 3 Shown; The compound M2 can be used as a hole transport material but not limited to this perovskite solar cell structure. The preparation process of perovskite solar cells is as follows: first, cut FTO conductive glass (15Ω / square, thickness 2.3mm) into small pieces of 1.5cm×2cm, and then use zinc powder and 2M hydrochloric acid to etch it according to the electrode pattern. After etching, the glass was ultrasonically cleaned with acetone and ethanol for ten minutes, dried with clean compressed air, and then annealed at 510°C for 30 minutes. Mix 7mL of isopropanol, 0.6mL of tetraisopropyl titanate and 0.4mL of acetone evenly, and then use nitrogen as the carrier gas to spray onto the FTO glass substrate heated at 450°C, heat for 20min and then cool...

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Abstract

The invention discloses a method for enhancing the molecular planarity of a non-helical organic small molecule hole transport material, which relates to the technical field of optoelectronic materials, and is to introduce a short-range intramolecular interaction. The present invention reduces the dihedral angle of adjacent groups in the molecule and enhances the planarity of molecules by introducing short-range intramolecular interactions into the molecule. Compared with molecules without short-range intramolecular interactions, the intermolecular interaction is effectively enhanced π-π stacking improves hole mobility.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a method for enhancing molecular planarity of a non-screw organic small molecule hole transport material. Background technique [0002] In recent years, organic-inorganic perovskite solar cells have achieved revolutionary development in the field of optoelectronics, and the highest photoelectric conversion efficiency (PCE) of the traditional front-mount device structure has exceeded 23.3%. Due to the limited hole-transporting ability of the perovskite layer itself, hole-transporting materials have become an integral part of perovskite solar cell (PSCs) devices. [0003] Currently, the most commonly used small organic molecule hole transport material is 2,2,7,7-tetrakis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobifluorene (spiro- OMeTAD) has many synthetic steps, harsh conditions, and complex purification process, resulting in high synthetic costs. In addition, in ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14H01L51/42H01L51/46
CPCH10K85/631H10K85/655H10K85/657H10K30/151H10K30/00Y02E10/549
Inventor 孔凡太孙媛彭耀乐
Owner HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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