Preparation method and application of a class of organic semiconductor materials based on polycyclic aromatic hydrocarbon k-position and imidazolyl groups

An organic semiconductor and polycyclic aromatic hydrocarbon technology, which is applied in the field of preparation of polycyclic aromatic hydrocarbon K-position imidazole-based organic semiconductor materials, can solve the problems that polycyclic aromatic hydrocarbon materials are rarely used in organic solar cells and the like, and is conducive to molecular stacking, The effect of short synthesis route and huge application prospect

Active Publication Date: 2019-05-03
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, PAH materials are rarely used in organic solar cells

Method used

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  • Preparation method and application of a class of organic semiconductor materials based on polycyclic aromatic hydrocarbon k-position and imidazolyl groups
  • Preparation method and application of a class of organic semiconductor materials based on polycyclic aromatic hydrocarbon k-position and imidazolyl groups
  • Preparation method and application of a class of organic semiconductor materials based on polycyclic aromatic hydrocarbon k-position and imidazolyl groups

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1. In a single-necked round-bottom flask (250 mL), phenanthrenequinone (3 g, 14 mmol), ammonium acetate (13.98 g, 181 mmol) and ethanol (100 mL) were added, and stirred at 78°C under reflux. Then, 2-thiophenecarbaldehyde (1.6 g, 14 mmol) was added to the reaction system. After the addition is complete, continue stirring at 78 degrees overnight. After the reaction, the ethanol was spin-dried, the solid was washed with water, filtered with suction, dried, and separated and purified on a silica gel column to obtain 1.48g of 2-thienyl-1H-phenanthroline [9,10-d]-imidazole (hereinafter referred to as TPh), yield 34.3%. 1H NMR (400MHz, DMSO) δ (ppm): 8.84 (d, J = 14.1, 8.3 Hz, 2H), 8.48 (d, J = 21.5, 7.7 Hz, 2H), 7.92 (d, J = 3.6 Hz, 1H ), 7.79-7.67 (m, 3H), 7.62 (d, J=6.7 Hz, 2H), 7.29-7.24 (m, 1H), 5.74 (s, 1H).

[0034] Add TPh (1.6g, 5.3mmol), potassium carbonate (3.68g, 26.7mmol), potassium iodide (0.044g, 0.3mmol) and N,N-dimethylformamide (hereinafter referred t...

Embodiment 2

[0038] Example 2. In a single-neck round bottom flask (250 mL), pyrene dione (4.5 g, 19 mmol), ammonium acetate (18.8 g, 244 mmol) and ethanol (100 mL) were added, and the mixture was refluxed and stirred at 78 degrees. Then, 2-thiophenecarbaldehyde (2.18 g, 19 mmol) was added to the reaction system. After the addition is complete, continue stirring at 78 degrees overnight. After the reaction, the ethanol was spin-dried, the solid was washed with water, filtered with suction, dried, and separated and purified on a silica gel column to obtain 2.15g of 10-(2-thienyl)-9H-pyrene[4,5-d]imidazole (hereinafter referred to as TPy). The yield was 34.2%. 1H NMR(400MHz,DMSO)δ(ppm): 8.76(d,J=7.5Hz,1H), 8.70(d,J=7.6Hz,1H), 8.26-8.08(m,7H),7.98(d,J = 3.6 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.32-7.28 (m, 1H).

[0039] Add TPy (2.0g, 6.2mmol), potassium carbonate (4.3g, 30.9mmol), potassium iodide (0.05g, 0.3mmol) and N,N-dimethylformamide (hereinafter referred to as DMF) (10 mL), stirred at ...

Embodiment 3

[0043] Example 3. TPh (1.0g, 3.3mmol), potassium carbonate (2.3g, 16.7mmol), potassium iodide (0.028g, 0.17mmol) and N,N-dimethylform were added to a two-necked round bottom flask (100mL) Amide (hereinafter referred to as DMF) (10 mL), stirred at room temperature. Then 1-bromooctane (0.83 g, 4.3 mmol) was added dropwise. After the addition is complete, react at room temperature overnight. After the reaction, it was extracted with water and dichloromethane, concentrated, and separated and purified by silica gel column to obtain 1.1g 1.1g of 1-octyl-2-thienyl-1H-phenanthrene[9,10-d]imidazole (hereinafter referred to as TPh-C8) ). The yield is 80%. 1H NMR(400MHz,CDCl3)δ(ppm)8.86-8.82(m,1H), 8.80(d,J=7.8Hz,1H), 8.69(d,J=8.3Hz,1H), 8.29-8.23(m, 1H), 7.74–7.60 (m, 4H), 7.58–7.51 (m, 2H), 7.23 (dd, J = 5.1, 3.6 Hz, 1H), 4.76–4.69 (m, 2H), 2.08 (d, J = 15.6, 7.8 Hz, 2H), 1.63 (s, 1H), 1.50-1.39 (m, 2H), 1.39-1.21 (m, 9H), 0.88 (d, J = 8.8, 5.0 Hz, 3H).

[0044] In a reaction flask ...

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Abstract

The invention discloses a preparation method and application of a polycyclic aromatic hydrocarbon K-position imidazole-based organic semiconductor material. The general structural formula of the synthesized material is as follows, wherein, Ar represents aryl and substituted aryl, and R represents the difference in length The characteristic of the structural design is that the benzene ring position of the imidazole connection belongs to the K position of polycyclic aromatic hydrocarbons, that is, the direction of the short axis of the molecule, which is completely different from the connection position (1, 2) of conventional compounds. In addition, the structural design of this type of compound conforms to the D-A-D (donor-acceptor-donor) structure, which can be well applied to organic solar cell devices and improve their device performance.

Description

Technical field [0001] The invention belongs to the field of organic functional materials, and specifically relates to a preparation method and application field of a class of polycyclic aromatic hydrocarbon K-position imidazole-based organic semiconductor materials. Background technique [0002] Since Shirakawa, MacDiarmid and Heeger discovered highly conductive polyacetylene in 1977, the π-conjugated system has attracted worldwide attention as a new material for the development and production of next-generation electronic devices (also known as organic electronics). In terms of definition, organic electronics is completely different from conventional inorganic electronics. Organic semiconductor materials have diverse structures, and their molecular structures can be combined with functional groups during design. At the same time, the diversity of this structure has opened a new era in the field of electronic device design. So far, scientists have discovered and synthesized a l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06H01L51/46
CPCC09K11/06C07D487/04C09K2211/1044C09K2211/1092H10K85/655H10K85/6572Y02E10/549
Inventor 汪联辉赵保敏翟柳青何聪王遂良傅妮娜
Owner NANJING UNIV OF POSTS & TELECOMM
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