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Hole transport material, and preparation method and application thereof

A technology of hole transport material and hole transport layer, applied in the field of solar cells, can solve the problems of serious environmental hazards, reduced battery stability, and high cost

Active Publication Date: 2020-05-29
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, PTAA and Spiro-OMeTAD are expensive and poor in conductivity; P-type dopants and lithium bistrifluoromethanesulfonimide (LiTFSI) need to be introduced during use to improve the conductivity of the hole transport layer
The use of dopants and additives not only reduces the stability of the battery, but also further increases the production cost of the battery
In addition, most of the current hole transport materials need to be processed with chlorinated aromatic hydrocarbon solvents such as chlorobenzene. These solvents are highly toxic and harmful to the environment, which is very unfavorable for the industrialization process of perovskite batteries.

Method used

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  • Hole transport material, and preparation method and application thereof
  • Hole transport material, and preparation method and application thereof
  • Hole transport material, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] This embodiment provides a hole transport material, which has the structure shown in Formula I-1:

[0082]

[0083] Synthetic route of hole transport material Ⅰ-1:

[0084]

[0085] (1) Synthesis of intermediate compound 1

[0086] 4-(4-Methoxyphenylamino)phenylboronic acid pinacol ester (226mg, 0.52mmol), 7-bromo-4-formylbenzo[C][1,2,5]thiadiazole ( 100mg, 0.4mmol), Pd (PPh 3 ) 4 (25mg, 0.04mmol), potassium carbonate (90mg, 0.6mmol), placed in a two-necked bottle; after pumping argon three times, add 7mL of tetrahydrofuran and 1mL of water; the reaction was carried out under the protection of argon; reacted at 100°C for 24h Finally, after the reaction was completed, the reaction system was cooled to room temperature, the solvent was spun out, and the initial product was purified by column to obtain intermediate compound 1 with a mass of 170 mg and a yield of 91%.

[0087] 1 H NMR (400MHz, CDCl3): δ10.75(s, 1H), 8.28(d, J=7.5Hz, 1H), 7.92(d, J=8.9Hz, 2H), 7.8...

Embodiment 2

[0096] This embodiment provides a hole transport material, which has the structure shown in Formula I-2:

[0097]

[0098] Synthetic route of hole transport material Ⅰ-2:

[0099]

[0100] (1) Synthesis of compound 2: 4,4'-dimethoxydiphenylamine (960mg, 4.2mmol), 2-bromo-5-iodofluorobenzene (1.56g, 5.25mmol), Pd 2 (dba) 3 (193mg, 0.21mmol), dppf (112mg, 0.18mmol), sodium tert-butoxide (2g, 21mmol), placed in a two-necked bottle; after pumping argon for three times, add anhydrous toluene 25mL; react under the protection of argon After reacting at 120° C. for 24 hours, the reaction system was cooled to room temperature, the solvent was spun out, and the initial product was further purified through a column to obtain compound 2 with a mass of 1.5 g and a yield of 89%.

[0101] 1 H NMR (400MHz, CDCl3): δ7.26-7.23 (m, 1H), 7.08 (d, J = 8.8Hz, 4H), 6.87 (d, J = 8.8Hz, 4H), 6.64 (dd, J = 11.4 ,2.5Hz,1H),6.56(dd,J=8.8,2.5Hz,1H),3.82(s,6H).

[0102] (2) Synthesis of Compound...

Embodiment 3

[0111] This embodiment provides a hole transport material, which has the structure shown in Formula I-3:

[0112]

[0113] The synthetic route of hole transport material Ⅰ-3:

[0114]

[0115] (1) Synthesis of Compound 5: Compound 5 was synthesized according to the method for compound 2 in Synthesis Example 2, with a yield of 72%.

[0116] 1 H NMR (400MHz, CDCl3): δ7.30-7.26 (m, 1H), 7.12 (d, J = 8.2Hz, 4H), 7.02 (d, J = 8.4Hz, 4H), 6.74 (dd, J = 11.2 ,2.6Hz,1H),6.66(dd,J=8.8,2.6Hz,1H),2.35(s,6H).

[0117] 19 F NMR (376MHz, CDCl3): δ-106.79.

[0118] (2) Synthesis of Compound 6: Compound 6 was synthesized according to the method for compound 3 in Synthesis Example 2, with a yield of 88%.

[0119] 1 H NMR (400MHz, CDCl3): δ7.54-7.50 (m, 1H), 7.12 (d, J = 8.1Hz, 4H), 7.04 (d, J = 8.3Hz, 4H), 6.71 (dd, J = 8.3 ,2.0Hz,1H),6.58(dd,J=12.2,1.9Hz,1H),2.35(s,6H),1.36(s,12H).

[0120] 19 F NMR (376MHz, CDCl3): δ-101.74.

[0121] (3) Synthesis of Compound 7: Compound 7 wa...

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Abstract

The invention provides a hole transport material, and a preparation method and an application thereof. The hole transport material has a structure represented by formula I in the specification. The hole transport material provided by the invention has good hole transport performance and excellent solubility, can even be dissolved and processed in some green solvents, can obtain good film morphology and controllable photoelectric properties, and can be applied to perovskite solar cells.

Description

technical field [0001] The invention belongs to the technical field of solar cells, and in particular relates to a hole transport material and its preparation method and application. Background technique [0002] In recent years, perovskite solar cells using organic-inorganic hybrid perovskite materials as "light harvesting agents" have achieved rapid development, which can convert solar energy into electrical energy at a lower cost, and have been favored by the global scientific research circle. Favored by the industrial circle, its energy conversion efficiency has gradually improved, and the recently verified efficiency has exceeded 25%. In perovskite solar cells, in addition to the active layer perovskite, the hole transport material is also very critical; the hole transport material can not only extract holes, but also transport holes, which is very important for improving the performance of the device. [0003] At present, most of the reported high-efficiency perovskit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/14C07D417/06H01L51/42
CPCC07D285/14C07D417/06H10K85/636H10K85/656H10K85/631H10K85/657H10K30/15H10K85/6572Y02E10/549
Inventor 郭旭岗王漾廖巧干
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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