Polycyclic aromatic hydrocarbon organic semiconductor material and preparation method and application thereof

A technology of organic semiconductors and polycyclic aromatic hydrocarbons, applied in the field of polycyclic aromatic hydrocarbons organic semiconductor materials and their preparation, can solve the problems of long synthesis steps, difficult synthesis, cumbersome operation, etc., and achieve easy separation, less by-products, and high mobility. Effect

Inactive Publication Date: 2018-09-14
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no matter what kind of linear polycyclic aromatic hydrocarbons are realized by high temperature or transition metal catalysis, the synthesis steps are long, the operation is cumbersome, and the yield is low. Simple synthesis with high selectivity

Method used

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  • Polycyclic aromatic hydrocarbon organic semiconductor material and preparation method and application thereof
  • Polycyclic aromatic hydrocarbon organic semiconductor material and preparation method and application thereof
  • Polycyclic aromatic hydrocarbon organic semiconductor material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] This example provides a method for preparing an angular molecular compound DTBCz with carbazole as the nucleus, and its synthetic route is as follows: figure 2 As shown, the finally obtained angular molecular structure with carbazole as the nucleus is as follows:

[0044]

[0045] The first step, take 14.9g (10mmol) of compound 1 (i.e. 3,6-dibromoalkylcarbazole), and dissolve compound 1 azole in 70mL of anhydrous tetrahydrofuran under the protection of nitrogen. Under protection, 8 mL (20 mmol) of butyl lithium with a concentration of 2.5 mol / L was added dropwise with a syringe, and kept stirring at low temperature for 1 h, and then 4.8 g (25 mmol) of 3-bromothiophene-2-carbaldehyde was added dropwise to continue the reaction. The reaction mixture was stirred at room temperature for 8 h and extracted with dichloromethane to obtain an organic phase. After drying the combined organic phases with sodium sulfate, the solvent was removed to obtain 3.6 g of a crude produc...

Embodiment 2

[0050] This example provides a preparation method for the angular molecular compound TDTBCz with carbazole as the nucleus, and its synthetic route is as follows image 3 As shown, the structural formula of the angular molecular compound TDTBCz with carbazole as the core finally obtained is:

[0051]

[0052] In the first step, 4.9g (10mmol) of compound 1 was dissolved in 70mL of anhydrous tetrahydrofuran under the protection of nitrogen, and 8mL of butyllithium solution with a concentration of 2.5mol / L was added using a syringe at a low temperature of -78°C and under the protection of nitrogen. (20mmol), kept stirring at low temperature for 1h, then added 6.18g (25mmol) of 3-bromo-2-formaldehyde-thiophene, and reacted to obtain a reaction mixture. After the reaction mixture was kept at room temperature for 8 h, the mixture was extracted with dichloromethane, the organic phase was taken, and the combined organic phase was dried over sodium sulfate. The solvent was then remo...

Embodiment 3

[0057] This example provides a method for preparing a horn-shaped molecular compound DTBCzC8 with carbazole as the nucleus, and its synthetic route is as follows Figure 4 As shown, the structural formula of the angular molecular compound DTBCzC8 with carbazole as the nucleus is obtained at last:

[0058]

[0059] In the first step, 5g (10mmol) of compound 1 was dissolved in 70mL of anhydrous tetrahydrofuran under the protection of nitrogen, and 8mL (20mmol) of butyllithium with a concentration of 2.5mol / L was added using a syringe under the protection of low temperature of -78°C. Keep stirring at low temperature for 1 h, then add 7.6 g (25 mmol) of 3-bromo-5-octylthiophene-2-carbaldehyde to obtain a reaction mixture. After the reaction mixture was stirred at room temperature for 8 h, it was extracted with dichloromethane, the organic phase was taken, and the combined organic phase was dried over sodium sulfate. The solvent was removed to obtain 3.3 g of the crude product ...

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Abstract

The invention relates to a preparation method of a polycyclic aromatic hydrocarbon organic semiconductor material, the preparation method comprises the following steps: 3,6-dibromoalkylcarbazole is dissolved in anhydrous diethyl ether or tetrahydrofuran, a lithium reagent is added dropwise and stirred, and an aromatic aldehyde solution is continuously added dropwise to obtain compound A; the compound A is dissolved in toluene or xylene, zinc iodide and sodium cyanoborohydride are added, and stirred to obtain compound B; the compound B is dissolved in absolute ethanol or tetrahydrofuran, a lithium reagent is added dropwise and stirred, and an anhydrous formylating reagent is added and stirred to obtain compound C; the compound C is dissolved in toluene or xylene, macroporous acidic ion exchange resin is added, and stirred to obtain the horn-type polycyclic aromatic hydrocarbon organic semiconductor material having a carbazole as a core. The organic semiconductor material has high stability and good solubility, and is applied to a field effect transistor device to exhibit hole migration characteristics which are not dependent on film thickness, and the preparation method is easy to repeat, and is advantageous for industrial production.

Description

technical field [0001] The invention relates to a polycyclic aromatic hydrocarbon organic semiconductor material and its preparation method and application, belonging to the technical field of organic thin film transistors. Background technique [0002] Organic semiconductor materials have the advantages of strong structure flexibility, solution processing and flexible substrate processing, and have become the main body of the new generation of electronic information materials. The research and development of a new type of highly efficient organic conjugated semiconductor material will have a broad market prospect in the electronics industry. Polycyclic aromatic hydrocarbons (Acenes) are widely used in photovoltaic cells (OPVs) and organic field-effect transistors (OFETs). Among all OFET materials, one-dimensional or two-dimensional fused ring (1D / 2DF Fusedacene or heteroacene) materials exhibit extremely high device mobility. For example, Pentacene (Pentacene), rubrene (R...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/14C07D495/22H01L51/05H01L51/30
CPCC07D495/14C07D495/22H10K85/657H10K10/46
Inventor 赵保敏胡月明仪明东傅妮娜刘书利黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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