A kind of silicon naphthalocyanine cathode interface material and preparation method and application thereof

A cathode interface and naphthalocyanine technology, which is applied in the field of silicon naphthalocyanine cathode interface materials and its preparation, can solve the problems of limiting the application of naphthalocyanine compounds, poor electron acceptance ability, and high LUMO energy level, and is conducive to large-scale Large production, lower work function, beneficial to the effect of separation and purification

Active Publication Date: 2022-07-05
NANCHANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although unmodified naphthalocyanine molecules have many advantages in organic photovoltaics, their solubility is poor, they cannot be processed by low-cost solutions, their LUMO energy level is high (-3.6eV), and their electron acceptance is poor. Used as a hole transport material (Angew.Chem., Int.Ed.2018, 57, 9885)
However, the conditions for preparing thin films by evaporation are harsh and the cost is high, which greatly limits the application of naphthalocyanine compounds.

Method used

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  • A kind of silicon naphthalocyanine cathode interface material and preparation method and application thereof
  • A kind of silicon naphthalocyanine cathode interface material and preparation method and application thereof
  • A kind of silicon naphthalocyanine cathode interface material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] The synthesis of compound 2a (amination of 6,7-dicyano-n-butyl-naphthalene monoimide (compound 1a)) is as follows:

[0070]

[0071] Under argon protection, compound 1a (1 g, 3.30 mmol), NaOCH was added to a 100 mL two-necked flask 3 (178 mg, 3.30 mmol), NH 3 (7M in CH 3OH, 33.0 mmol), methanol (30 mL), reacted at 65 °C for 45 min, and cooled to room temperature. The reactant was settled in 45 mL of water and filtered with suction to obtain a white solid. Column separation was carried out with a mixed solvent of dichloromethane and methanol (25 / 1, v / v) as the eluent to obtain a white solid 2a with a yield of 695 mg and a yield of 66.08%.

[0072] 1 H NMR (400MHz, CDCl 3 )δ8.35(d,4H),4.23(m,2H),2.12(m,2H),1.23(m,2H),0.81(m,3H)ppm.

[0073] 13 C NMR (101MHz, d 6 -DMSO)δ167.7,137.66,137.3,134.1,134.2,129.4,129.2,126.4,125.6,124.4,123.4,52.3,26.4,22.1,14.1ppm.

[0074] HRMS(MALDI-TOF):Calcd for C 18 H 16 N 4 O 2 Exact Mass: 320.1273, found: 320.1245 (M + )...

Embodiment 2

[0076] The synthesis of compound 2b (amination of 6,7-dicyano-(6-undecyl)naphthalene monoimide (compound 1b)) is as follows:

[0077]

[0078] Under argon protection, compound 1b (1 g, 2.49 mmol), NaOCH was added to a 100 mL two-necked flask 3 (269 mg, 4.98 mmol), NH 3 (7M in CH 3 OH, 24.9 mmol), methanol (30 mL), reacted at 65 °C for 30 min, and cooled to room temperature. The reactant was settled in 30 mL of water and filtered with suction to obtain a white solid. Column separation was carried out with a mixed solvent of dichloromethane and methanol (50 / 1, v / v) as the eluent to obtain a white solid 2b with a yield of 711 mg and a yield of 68.11%.

[0079] 1 H NMR (400MHz, CDCl 3 )δ8.38(d,J=19.3Hz,4H),4.26(m,1H),2.09(m,2H),1.74(m,2H),1.24(m,12H),0.81(m,6H)ppm .

[0080] 13 C NMR (101MHz, d 6 -DMSO)δ167.8,137.8,137.4,134.2,134.0,129.3,129.2,126.5,125.9,124.8,123.9,52.1,32.1,31.3,26.1,22.4,14.2ppm.

[0081] HRMS(MALDI-TOF):Calcd for C 25 H 30 N 4 O 2 Exact Mas...

Embodiment 3

[0082] Example 3: Synthesis of Compound 2c

[0083]

[0084] Under argon protection, compound 1c (0.81 g, 2.00 mmol), NaOCH was added to a 100 mL two-necked flask 3 (538 mg, 10 mmol), NH 3 (7M in CH 3 OH, 2 mmol), methanol (30 mL), reacted at 50 °C for 30 min, and cooled to room temperature. The reactant was settled in 30 mL of water and filtered with suction to obtain a white solid. Column separation was carried out using a mixed solvent of dichloromethane and methanol (50 / 1, v / v) as eluent to obtain a white solid 2c with a yield of 510 mg and a yield of 60.15%.

[0085] HRMS(MALDI-TOF):Calcd for C 26 H 24 N 4 O 2 Exact Mass: 424.1899, found: 424.2860 (M + ).

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Abstract

A silicon naphthalocyanine cathode interface material and a preparation method and application thereof belong to the technical field of optoelectronic materials. This silicon naphthalocyanine cathode interface material enhances the electron-withdrawing ability of molecules by introducing imide groups into the periphery of naphthalocyanine; nitrogen-terminated alkyl groups can effectively improve the solubility of molecules in common organic solvents; axial use Four-coordinated silicon atoms, introducing multiple tertiary amines or quaternary ammonium salts with self-doping effect, effectively increase the solubility of the molecule in alcohol, and enhance the ability of the molecule to improve the work function and conductivity of the metal electrode. This kind of naphthalocyanine imide molecule is used as an interface layer in organic solar cells, and the photoelectric conversion efficiency is significantly improved.

Description

technical field [0001] The invention belongs to the technical field of optoelectronic materials, and more particularly relates to a silicon naphthalocyanine cathode interface material and a preparation method and application thereof. Background technique [0002] With the development of society, the demand for clean, pollution-free and renewable energy is becoming more and more urgent. As a device that can efficiently convert solar energy into electrical energy, solar cells have developed rapidly in recent years. Compared with expensive and bulky inorganic solar cells, organic solar cells have the advantages of low manufacturing cost, light weight, good flexibility, and large manufacturing area. With the successful development of a series of active layer materials with excellent performance, organic solar cells (OSCs) have made remarkable progress in the past few decades, and the cell conversion efficiency (PCE) has exceeded 18% (Joule 2019, 3, 1140; Sci .Bull.2020, 65, 27...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10H01L51/46H01L51/44
CPCC07F7/10H10K85/40H10K30/81Y02P70/50
Inventor 赵晓宏蔡春生袁忠义付居标黄国荣胡昱李磊马俊杰
Owner NANCHANG UNIV
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