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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, high LUMO energy level, and poor electron acceptance ability, and achieve favorable scale Large-scale production, beneficial to separation and purification, and the effect of reducing work function

Active Publication Date: 2021-10-08
NANCHANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology describes how certain materials have been found useful when mixed with other chemical substances like salts. These mixtures help create interfaces between different compounds without losing their original properties such as absorption spectra due to changes made during manufacturing processes. Additionally, these compositions allow for easier removal of impurity atoms while maintaining desired characteristics. Overall, they make possible new ways to improve electronic device performance through modifying metals' surfaces.

Problems solved by technology

This patented technical problem addressed in this patents relates to improving the transferring properties of photoactive components from one substrate to another when converting sunlight into electrical current through interfaces between different parts of these components. Current methods involve modifying certain chemical structures on surfaces like ammonium salts or pigments which affect their ability to absorb incident rays and transmit charges. These modifications require complicated processes involving multiple steps, leading to decreased production rates and increased costs associated therewith. Additionally, existing methods often result in reduced electronic mobilities of the component's surface areas, making effective utilization challenges.

Method used

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  • Silicon naphthalocyanine cathode interface material and preparation method and application thereof
  • Silicon naphthalocyanine cathode interface material and preparation method and application thereof
  • Silicon naphthalocyanine cathode interface material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Synthesis of Compound 2a (6,7-dican-n-butyl-naphthalimide (compound 1a) is as follows:

[0070]

[0071] Under argon protection, Compound 1a (1 g, 3.30 mmol) is added to 100 ml of two bottles, NAOCH 3 (178mg, 3.30mmol), NH 3 (7m in ch 3OH, 33.0 mmol), methanol (30 mL), after 45 min at 65 ° C, cooled to room temperature. The reactants were settled in 45 mL of water, filtered to give a white solid. The column separation was carried out with dichloromethane and methanol (25 / 1, v / v) mixed solvent, and the white solid 2a was 695 mg, and the yield was 66.08%.

[0072] 1 H NMR (400MHz, CDCL 3 Δ8.35 (D, 4H), 4.23 (m, 2H), 2.23 (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, 14.1 ppm.

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

Embodiment 2

[0076] The synthesis of Compound 2B (6,7-dicano-(6-decolina) naphthalimide (compound 1b) is as follows:

[0077]

[0078] Under argon protection, Compound 1b (1 g, 2.49 mmol) is added to 100 ml of two bottles, Naoch 3 (269mg, 4.98mmol), NH 3 (7m in ch 3 OH, 24.9 mmol), methanol (30 mL), reacted at 65 ° C for 30 min, cooled to room temperature. The reactants were settled in 30 mL of water, filtered to give a white solid. The column separation was carried out with dichloromethane and methanol (50 / 1, v / v) mixed solvent, and the white solid 2b was obtained, the yield was 711 mg, and the yield was 68.1%.

[0079] 1 H NMR (400MHz, CDCL 3 Δ8.38 (D, J = 19.3 Hz, 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, 14.2 ppm.

[0081] HRMS (MALDI-TOF): Calcd for C 25 Hide 30 N 4 O 2 Exact Mass: 418.2369, Found: 418....

Embodiment 3

[0082] Example 3: Synthesis of Compound 2C

[0083]

[0084] Under argon protection, Compound 1C (0.81 g, 2.00 mmol) is added to 100 ml of two bottles, Naoch 3 (538mg, 10mmol), NH 3 (7m in ch 3 OH, 2 mmol), methanol (30 mL), reacted at 50 ° C for 30 min, cooled to room temperature. The reactants were settled in 30 mL of water, filtered to give a white solid. The column separation was carried out with dichloromethane and methanol (50 / 1, v / v) mixed solvent, and the white solid 2c was obtained, the yield was 510 mg, and the yield was 60.15%.

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

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Abstract

The invention discloses a silicon naphthalocyanine cathode interface material and a preparation method and application thereof, belonging to the technical field of photoelectric materials. According to the silicon naphthalocyanine cathode interface material, an imide group is introduced to the periphery of naphthalocyanine, so the electron withdrawing capability of molecules is enhanced; the solubility of the molecules in a common organic solvent can be effectively improved through nitrogen-terminated alkyl groups; tetra-coordinated silicon atoms are adopted in an axial direction, a plurality of tertiary amine or quaternary ammonium salts with self-doping effect are introduced, so the solubility of molecules in alcohol is effectively improved, and the metal electrode work function improving capacity and conductivity of the molecules are enhanced; and the naphthalocyanine imide molecules are applied to an organic solar cell as an interface layer for the first time, and photoelectric conversion efficiency is obviously improved.

Description

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Claims

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Application Information

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Owner NANCHANG UNIV
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