Preparation method and application of polycyclic aromatic hydrocarbon K-position imidazolyl-based organic semiconductor materials

A technology of organic semiconductors and polycyclic aromatic hydrocarbons, which is applied in the field of preparation of polycyclic aromatic hydrocarbons based on K-position and imidazole-based organic semiconductor materials, can solve the problem that polycyclic aromatic hydrocarbons materials are rarely used in organic solar cells, etc., to achieve molecular stacking, Great application prospects and good stability

Active Publication Date: 2016-08-03
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • 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 polycyclic aromatic hydrocarbon K-position imidazolyl-based organic semiconductor materials
  • Preparation method and application of polycyclic aromatic hydrocarbon K-position imidazolyl-based organic semiconductor materials
  • Preparation method and application of polycyclic aromatic hydrocarbon K-position imidazolyl-based organic semiconductor materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1. In a single-necked round bottom flask (250mL), add phenanthrenequinone (3g, 14mmol), ammonium acetate (13.98g, 181mmol) and ethanol (100mL), and stir under reflux at 78 degrees. Then, 2-thiophenecarbaldehyde (1.6 g, 14 mmol) was added to the reaction system. After the dropwise addition, continue to stir overnight at 78°C. After the reaction was finished, the ethanol was spin-dried, the solid was washed with water, then suction-filtered, dried, and separated and purified on a silica gel column to obtain 1.48g of 2-(thiophen-2-yl)-1H-phenanthro[9,10-d]imidazole (hereinafter referred to as TPh), producing rate 34.3%. 1 HNMR (400MHz, DMSO) δ (ppm): 8.84 (d, J = 14.1, 8.3Hz, 2H), 8.48 (d, J = 21.5, 7.7Hz, 2H), 7.92 (d, J = 3.6Hz, 1H) , 7.79–7.67 (m, 3H), 7.62 (d, J=6.7Hz, 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 referre...

Embodiment 2

[0038] Example 2. In a single-necked round bottom flask (250mL), add pyrenedione (4.5g, 19mmol), ammonium acetate (18.8g, 244mmol) and ethanol (100mL), and stir under reflux at 78 degrees. Then, 2-thiophenecarbaldehyde (2.18 g, 19 mmol) was added to the reaction system. After the dropwise addition, continue to stir overnight at 78°C. After the reaction, the ethanol was spin-dried, the solid was washed with water, then suction-filtered, dried, and separated and purified on a silica gel column to obtain 2.15 g of 10-(thiophen-2-yl)-9H-pyreno[4,5-d]imidazole (hereinafter referred to as TPy). The rate is 34.2%. 1 HNMR (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 = 3.6Hz, 1H), 7.74 (d, J = 5.0Hz, 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 room temperature. ...

Embodiment 3

[0043] Embodiment 3. in two-necked round bottom flask (100mL), add TPh (1.0g, 3.3mmol), potassium carbonate (2.3g, 16.7mmol), potassium iodide (0.028g, 0.17mmol) and N,N-dimethyl form 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 dropwise addition was completed, the reaction was carried out overnight at room temperature. After the reaction, extract with water and dichloromethane, concentrate, and separate and purify on a silica gel column to obtain 1.1g of 1-octyl-2-(thiophen-2-yl)-1H-phe-nanthro[9,10-d]imidazole (hereinafter referred to as TPh -C 8 ). Yield 80%. 1 HNMR (400MHz, CDCl 3)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=5.1,3.6Hz,1H),4.76–4.69(m,2H),2.08(d,J=15.6,7.8Hz,2H ), 1.63 (s, 1H), 1.50–1.39 (m, 2H), 1.39–1.21 (m, 9H), 0.88 (d, J=8.8, 5.0Hz, 3H).

[0044] In the reaction flask (50mL...

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Abstract

The invention discloses a preparation method and an application of polycyclic aromatic hydrocarbon K-position imidazolyl-based organic semiconductor materials. The structural general formula of the synthesized materials is shown in the description; and in the general formula, Ar represents an aryl group or a substituted aryl group, and R represents an alkyl chain with non-uniform lengths. The structural design of the materials is characterized in that the position of a phenyl ring connected with imidazole belongs to a K(4,5) position, and the above connection is completely different from the connecting position (1,2) of routine compounds. The structural design of like compounds accords with a D-A-D (donor-acceptor-donor) structure, and can be well applied to organic solar battery devices to improve the performances of the devices.

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). By definition, organic electronics is completely different from conventional inorganic electronics. Organic semiconductor materials have a variety of structures, and their molecular structures can be combined with functional groups when they are designed. At the same time, this structural diversity opens up a new era in the design of electronic devices. So far, scientists have discovered and synthesized a larg...

Claims

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Application Information

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Patent Type & Authority Applications(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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