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Organic hole transport material taking tetrathienopyrrole as core as well as preparation method and application thereof

A hole transport material, phenopyrrole technology, applied in the field of solar cells, can solve the problems of low efficiency, complex synthesis, poor stability, etc., achieve good dissolution and film-forming performance, simple synthesis route, and improve efficiency

Active Publication Date: 2019-01-15
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although some progress has been made, there are still many problems in the organic hole materials used in PSCs: such as complex synthesis, high cost, poor stability and low battery efficiency, etc.

Method used

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  • Organic hole transport material taking tetrathienopyrrole as core as well as preparation method and application thereof
  • Organic hole transport material taking tetrathienopyrrole as core as well as preparation method and application thereof
  • Organic hole transport material taking tetrathienopyrrole as core as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of Organic Hole Transport Material (4)

[0028] The synthetic route is as follows:

[0029]

[0030] The raw material (1) used in this example was prepared and synthesized according to the patent (authorization number: ZL 201610828658.0); the raw material (3) was prepared according to the literature Rakstys, K.; Abate, A.; Ibrahim Dar, M.; Gao, P.; Jankauskas, V.; Jacopin, G.; Kamarauskas, E.; Kazim, S.; Ahmad, S.; M.; Nazeeruddi, M.K.J.Am.Chem.Soc.2015, 137, 16172-16178. Prepared; other reagents can be obtained commercially.

[0031] The synthesis of formula (2) compound:

[0032] Add 636mg of raw material (1) and 20mL of tetrahydrofuran to a 100mL single-necked round-bottomed flask under ice-bath conditions, then add 392mg of N-bromosuccinimide in batches to the system, at 25°C, in the dark Reaction for 8 hours; quenched with water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to remove th...

Embodiment 2

[0036] The synthesis of formula (2) compound:

[0037] Add 636mg of raw material (1) and 20mL of N,N-dimethylformamide to a 100mL single-necked round-bottom flask under ice-bath conditions, and then add 374mg of N-bromosuccinimide in batches to the system , at 25°C, reacted in the dark for 8h; quenched with water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and distilled off the solvent under reduced pressure; the crude product was subjected to column chromatography (eluent: petroleum ether / dichloromethane = 25 / 1~15 / 1) to obtain 650 mg of the compound represented by formula (2) as a white solid with a yield of 82%.

[0038] Synthesis of Organic Hole Transport Material (4):

[0039] Under the protection of argon, in a 100mL three-necked round-bottomed flask, 397mg of the compound shown in formula (2), 495mg of the compound shown in formula (3), 29mg of tetrakistriphenylphosphine palladium, 690mg of potassium phosphate (2M) and 15mL of N,N-dimethylfor...

Embodiment 3

[0041] The organic hole transport (4) prepared in Example 1 or 2 was tested by thermogravimetric analysis (TGA). The test temperature range was 0-800°C, and the heating rate was 5°C / min. The test results (see figure 1 ) shows that its thermal decomposition temperature is 390°C, indicating that it has good thermal stability.

[0042] The hole transfer efficiency of organic holes (4) was tested by space charge limited current (SCLC) method. The relationship between hole transfer efficiency, current density and bias voltage is as follows: μ=8d 3 J / 9ε 0 ε r V 2 , where d is the hole film thickness (cm), J is the current density (mA / cm 2 ),ε 0is the vacuum dielectric constant (8.85×10 -14 C V -1 cm -1 ),ε r is a constant 3, and V is the setting bias voltage (V). The hole transfer efficiency of organic holes (4) calculated according to the test and formula is 2.18×10 - 4 cm 2 V -1 S -1 .

[0043] The organic hole transport (4) prepared in embodiment 1 or 2, its scann...

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Abstract

The invention discloses a new hole transport material taking tetrathienopyrrole as a core and methoxyl substituted triphenylamine as a peripheral modifying group and a preparation method and application thereof, and belongs to the field of application of perovskite solar cells. The new hole transport material is simple in synthetic route and easily available in raw materials, and has relatively high photo-thermal stability and hole migration efficiency. The new hole transport material is applied to perovskite solar cells, results show that the highest photoelectric conversion efficiency of 16.62% can be obtained, and the new hole transport material has a relatively good application prospect.

Description

technical field [0001] The invention belongs to the technical field of solar cells, and in particular relates to an organic hole transport material with tetrathienopyrrole as the core and its preparation and application. Background technique [0002] As a new generation of photovoltaic technology, perovskite solar cells (Perovskite Solar Cells, referred to as PSCs. Kojima A.; Teshima K.; Shirai Y.; et al.J.Am.Chem.Soc.2009,131,6050-6051) With the advantages of easy modulation of materials, high efficiency, simple preparation process, and low cost, it has become the most eye-catching new star in solar cells in recent years, and its development is extremely rapid. At present, the highest photoelectric conversion efficiency has exceeded 20% (Saliba, M.; Orlandi , S.; Matsui, T.; Aghazada, S.; et al. Nat. Energy 2016, 1, 15017-15023.). As an important part of PSCs, the hole transport layer is mainly used to collect and transport the holes injected by the perovskite absorber lay...

Claims

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Application Information

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IPC IPC(8): C07D495/22H01L51/42H01L51/46
CPCC07D495/22H10K85/657H10K30/00Y02E10/549
Inventor 梁茂王志辉吴云根孙喆薛松
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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