Conjugated compound, and organic thin film and organic thin film element each comprising same
A technology of organic thin films and compounds, applied in the field of organic thin films and organic thin film elements, can solve the problems such as the inability to utilize organic n-type semiconductors
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Embodiment 1
[0204]
[0205] Compound H (6 mg, 0.0127 mmol), malononitrile (15 mg, 0.227 mmol), ammonium acetate (2 mg, 0.0254 mmol) in absolute ethanol (1 mL) was refluxed at 80° C. for 30 minutes in a 20 mL eggplant-shaped flask. After naturally cooling to room temperature, water was added, and the solution was acidified with concentrated hydrochloric acid. The resulting solid was filtered with suction and washed with water. The obtained solid was analyzed by GPC (CHCl 3 ) was purified to obtain conjugated compound I (3 mg, yield 25%) represented by formula (33).
[0206] The evaluation results of the obtained conjugated compound I are shown below. In addition, as a result of CV measurement of the obtained conjugated compound I, a reversible reduction wave was observed at -0.76V, the LUMO energy level was lowered, and it was confirmed that it had excellent electron transport properties.
[0207] TLC R f =0.55 (CHCl 3 ); 1 H-NMR (400MHz, CDCl 3 )δ0.88-0.90 (m, 6H), 1.29-1.50 (m, ...
Embodiment 2
[0222]
[0223] Compound K (30 mg, 0.0425 mmol), malononitrile (17 mg, 0.255 mmol), ammonium acetate (7 mg, 0.0850 mmol) in absolute ethanol (1 mL) was refluxed at 80°C for 30 minutes in a 20 mL eggplant-shaped flask. After naturally cooling to room temperature, water was added, and the solution was acidified with concentrated hydrochloric acid. The resulting solid was filtered with suction and washed with water. The obtained solid was analyzed by GPC (CHCl 3 ) to obtain the conjugated compound L represented by formula (36) (11 mg, yield 29%).
[0224] The evaluation results of the obtained conjugated compound L are shown below. In addition, as a result of CV measurement of the obtained conjugated compound L, a reversible reduction wave was observed at -0.67V, the LUMO energy level was lowered, and it was confirmed that it had excellent electron transport properties.
[0225] TLC R f =0.69 (CHCl 3 )
[0226] 1 H-NMR (400MHz, CDCl 3 )δ0.80-0.96 (m, 6H), 1.25-1.44 (m, ...
Embodiment 3
[0230]
[0231] A low-resistance silicon wafer (as a gate electrode / insulating layer) with a thermal oxide film (silicon oxide film) is immersed in ethanol, distilled water, and acetone in sequence, and ultrasonically cleaned. Thereafter, the silicon wafer was subjected to UV-ozone cleaning to obtain a substrate having a hydrophilic surface. This substrate was immersed in hexamethyldisilazane:chloroform at room temperature, and ultrasonically cleaned with chloroform to obtain a surface-treated substrate.
[0232] Then, a coating solution in which the conjugated compound I obtained in Example 1 was dissolved in chloroform was prepared. This solution was deposited on a surface-treated substrate by a spin coating method to form an organic thin film. On this organic thin film, a gold electrode (source electrode, drain electrode) was formed by vacuum evaporation using a metal mask to fabricate an organic thin film transistor.
[0233] For the obtained organic thin film transist...
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