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Benzothiadiazole-based multi-arm conjugated molecules as well as preparation method and application thereof

A technology of benzothiadiazole and conjugated molecules, which is applied in the field of multi-arm conjugated molecules based on bibenzothiadiazole and its preparation and application, can solve the problem of affecting the service life of devices, reducing luminous efficiency, and increasing production Cost and other issues, to achieve the effect of good thermal stability, good solubility, good processability

Active Publication Date: 2012-07-25
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method of doping has achieved good results, there are great defects in this method: 1) the concentration of the guest should be precisely controlled, generally not higher than 5% of the host material, which brings great problems to the large-scale preparation of devices. It is inconvenient and increases production costs; 2) The host-guest material will undergo phase separation during the processing process, such as heat treatment, which will increase the distance between the host-guest, thereby making the energy transfer insufficient, thereby affecting the service life of the device; 3) Commonly used guest materials include heavy metals, which will cause triplet-triplet quenching at high current densities, resulting in low luminous efficiency (S.Chen, X.Xu, Y.Liu, G.Yu, X. Sun, W. Qiu, Y. Ma, "Synthesis and Characterization of n-TypeMaterials for Non-Doped Organic Red-Light-Emitting Diodes", Adv. Funct. Mater., 2005, 15, 1541; W-C. Wu, H-C. Yeh, L-H, Chan, C-T Chen, "Red Organic Light-Emitting Diodes with a Non-doping Amorphous Red Emitter", Adv. Mater., 2002, 14, 1072; Q-X. Tong, S-L. Lai, M-Y. Chan, Y-C. Zhou, H-L.Kwong, C-S.Lee, S-T.Lee, "Highly Efficient Blue Organic Light-Emitting Device Based on a Nondoped Electroluminescent Material", Chem.Mater., 2008, 20, 6310.)

Method used

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  • Benzothiadiazole-based multi-arm conjugated molecules as well as preparation method and application thereof
  • Benzothiadiazole-based multi-arm conjugated molecules as well as preparation method and application thereof
  • Benzothiadiazole-based multi-arm conjugated molecules as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] The synthetic route of small molecule 1 is as follows.

[0063]

[0064] (1)1a

[0065] Add bibenzothiadiazole (540mg, 2mmol) and 8ml hydrobromic acid to a 50ml single-necked bottle, slowly add liquid bromine (1.92g, 12mmol, dissolved in 6ml hydrobromic acid) at room temperature, after the addition, 110 °C reflux for one day. After cooling to room temperature, the suspension was washed with saturated sodium bisulfite solution to remove excess bromine, filtered, the solid was washed with a large amount of water, dried and purified by silica gel column chromatography to obtain light yellow solid 1a (279 mg, 40%). 1 H NMR (400MHz, CDCl 3 ): δ8.13(s, 1H), 8.11(d, J=8.9Hz, 1H), 8.06(d, J=8.9Hz, 1H), 7.78(d, J=8.9Hz, 1H), 7.70(d , J=8.9Hz, 1H). EI-MS: 347.9141; Calculated value: 347.9139. Elemental analysis calculated value (C 12 h 5N 4 S 2 Br): C, 41.27; H, 1.44; N, 16.04. Found: C, 41.12; H, 1.82; N, 16.00%.

[0066] (2)1b

[0067] Add 1a (942mg, 2.7mmol), 3-dod...

Embodiment 2

[0074] The synthetic route of small molecule 2 is as follows

[0075]

[0076] (1)2a

[0077] Add 2-bromo-3-dodecylthiophene (993mg, 3mmol), triphenylamine monotin (2.4g, 4.5mmol) and 20ml toluene solution in the 50ml two-necked bottle, after purging the air in the reaction vessel with nitrogen, add Tetrakis(triphenylphosphine)palladium (115mg, 0.1mmol), reflux at a temperature of 100-120°C for 48 hours, cool to room temperature, add excess potassium fluoride solution relative to the molar amount of triphenylamine monotin in the container and stir for 2 Hour. The organic phase was extracted with chloroform, washed twice with water, dried over anhydrous magnesium sulfate, spin-dried to dry the solvent, and purified by silica gel column chromatography to obtain light yellow oily liquid 2a (1.29 g, 87%). EI-MS: 495.2964, Calculated: 495.2960.

[0078] (2)2b

[0079] Add 2a (495mg, 1mmol) and 10ml dry tetrahydrofuran solution into a 50ml three-necked flask, cool to -78°C, v...

Embodiment 3

[0086] The synthetic route of small molecule 3 is as follows

[0087]

[0088] (1)3a

[0089] Add bibenzothiazole (540mg, 2mmol) and 8ml of hydrobromic acid into a 50ml single-necked bottle, slowly add liquid bromine (1.92g, 12mmol, dissolved in 6ml of hydrobromic acid) at room temperature, after the addition, reflux at 110°C One day, liquid bromine (1.92 g, 12 mmol, dissolved in 6 ml of hydrobromic acid) was then added, and the reaction was continued for one day. After cooling to room temperature, the suspension was washed with saturated sodium bisulfite solution to remove excess bromine, filtered, the solid was washed with plenty of water, dried and purified by silica gel column chromatography to give 3a (355 mg, 35%) as a pale yellow solid. 1 H NMR (400MHz, CDCl 3 ): δ 8.10 (d, J=9.0 Hz, 1H), 7.84 (s, 1H), 7.57 (d, J=9.0 Hz, 1H). EI-MS: 507.7310, Calculated: 507.7308. Elemental analysis calculated value (C 12 h 3 N 4 S 2 Br 3 ): C, 28.43; H, 0.60; N, 11.05. Found...

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Abstract

The invention relates to benzothiadiazole-based multi-arm conjugated molecules as well as a preparation method and applications thereof as an active layer material in organic semiconductor devices such as an organic light emitting diode (OLED), an organic photovoltaic (OPV) and an organic field effect transistor (OFET). The benzothiadiazole-based multi-arm conjugated small molecules in the invention have higher luminous efficiency, better sunlight capture capability and hole transmission capability, and good solution processability and thermal stability, are ideal materials for organic semiconductor devices, such as the OLED, the OPV, the OFET and the like, and have the structure as shown in the general formula disclosed in the specification.

Description

technical field [0001] The present invention relates to a class of bibenzothiadiazole-based multi-arm conjugated molecules and a preparation method thereof, and the use of such molecules as active layer materials in organic semiconductor devices such as organic light-emitting diodes (OLEDs), organic solar cells (OPVs) and Applications in Organic Field Effect Transistors (OFETs). Background technique [0002] The development of organic semiconductors has a history of more than 30 years. Compared with traditional inorganic semiconductor devices, the devices made of them have the following advantages: low cost, ultra-thin, light weight, simple manufacturing process, and large-area preparation, etc. . In view of these advantages, there is great interest in the study of organic semiconductors. The research on organic semiconductors generally includes the design and synthesis of semiconductor materials and the preparation of devices. Organic semiconductor devices mainly include...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14C09K11/06H01L51/54H01L51/46H01L51/30
CPCY02E10/549
Inventor 占肖卫汪海风朱道本
Owner INST OF CHEM CHINESE ACAD OF SCI
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