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Donor-receptor type organic semiconductor material with removable group anthracene unit and preparation method of donor-receptor type organic semiconductor material

A technology of organic semiconductors and groups, applied in the field of donor-acceptor organic semiconductor materials and preparation, can solve the problems of planarity damage of conjugated units, reduce the performance of organic semiconductor devices, reduce the charge transport capacity of materials, etc., and achieve good results. Photoelectric properties, excellent charge transport properties, good solubility effects

Inactive Publication Date: 2015-04-08
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the alkyl side chain with a large steric hindrance will destroy the original planarity of the conjugated unit, so that the obtained organic semiconductor material cannot form a tight molecular packing and an ordered molecular arrangement in the solid state, thereby reducing the charge of the material. transport capability, ultimately degrading the performance of organic semiconductor devices

Method used

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  • Donor-receptor type organic semiconductor material with removable group anthracene unit and preparation method of donor-receptor type organic semiconductor material
  • Donor-receptor type organic semiconductor material with removable group anthracene unit and preparation method of donor-receptor type organic semiconductor material
  • Donor-receptor type organic semiconductor material with removable group anthracene unit and preparation method of donor-receptor type organic semiconductor material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Preparation of Bilateral Boronate Products with Removable Group Anthracene Units 3

[0057] The synthetic route is as follows:

[0058]

[0059] (1) Synthesis of Compound 1

[0060] 40 mL of toluene was added to 2,6-dibromoanthracene (3.36 g, 10 mmol) and maleic anhydride (3.43 g, 35 mmol), and the reaction solution was heated to reflux for 24 hours. Cooled to room temperature, the reaction solution was extracted with ethyl acetate, the obtained organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed by a rotary evaporator to obtain a viscous liquid product, which was directly used in the next reaction without separation and purification.

[0061] (2) Synthesis of compound 2

[0062] Compound 1 (4.66 g, 10 mmol) was dissolved in 20 mL of methanol, about 1 mL of concentrated sulfuric acid was added thereto, and the reaction solution was heated and refluxed for 24 hours. Cooled to room temperature, extracted with ethyl acetate, the obta...

Embodiment 2

[0067] Preparation of Polymer PCOA8OTBT Based on Removable Group Anthracene

[0068] The synthetic route is as follows:

[0069]

[0070] Compound 4 was synthesized with reference to literature (Macromolecules, 2010, 43, 9771.)

[0071] Compound 3 (57.4 mg, 0.1 mmol), compound 4 (71.4 mg, 0.1 mmol) and two drops of trioctylmethylammonium chloride were added to a 25 mL round bottom flask and charged with nitrogen for 20 minutes. Palladium acetate (4 mg) and tris(4-methoxyphenyl)phosphine (20 mg) were added to the reaction flask, and nitrogen gas flow was continued for 20 minutes. Aqueous sodium carbonate (2M, 1 mL) and toluene (4 mL) were added to the reaction flask. The reaction solution was heated to 110°C and reacted for 4 hours, cooled to room temperature, and the reaction was dropped into methanol for precipitation, filtered to obtain a solid, which was extracted with acetone, n-hexane, and chloroform by a Soxhlet extractor in turn, and the chloroform was partially co...

Embodiment 3

[0081] Preparation of Polymer PCOA12OTBT Based on Removable Group Anthracene

[0082] The synthetic route is as follows:

[0083]

[0084] Compound 5 was synthesized with reference to literature (Macromolecules, 2010, 43, 9771.)

[0085] Compound 3 (57.4 mg, 0.1 mmol), compound 5 (82.7 mg, 0.1 mmol) and two drops of trioctylmethylammonium chloride were added to a 25 mL round bottom flask and charged with nitrogen for 20 minutes. Palladium acetate (4 mg) and tris(4-methoxyphenyl)phosphine (20 mg) were added to the reaction flask, and nitrogen gas flow was continued for 20 minutes. Aqueous sodium carbonate (2M, 1 mL) and toluene (4 mL) were added to the reaction flask. The reaction solution was heated to 110°C and reacted for 4 hours, cooled to room temperature, and the reaction was dropped into methanol for precipitation, filtered to obtain a solid, which was extracted with acetone, n-hexane, and chloroform by a Soxhlet extractor in turn, and the chloroform was partially c...

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Abstract

The invention discloses a donor-receptor type organic semiconductor material with a removable group anthracene unit, which is an alternating copolymer of an anthracene donor unit after ring-opening addition and other electorn-deficient units. According to the donor-receptor type organic semiconductor material, under a warming condition, an anthracene ring-opening addition unit can generate retro-diels-alder reaction. The invention further discloses a preparation method of the donor-receptor type organic semiconductor material with the removable group anthracene unit. The donor-receptor type organic semiconductor material keeps compact and ordered molecular stacking under a solid state while having good solution machinability, and has relatively high charge transmitting capability. The donor-receptor type organic semiconductor material can be applied to various organic photoelectric devices such as organic electroluminescence, organic photovoltaics and field effect transistors by serving as an active layer, an interface layer and the like, and is one kind of materials with commercial application prospect.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a donor-acceptor type organic semiconductor material with an anthracene unit of a detachable group and a preparation method thereof. Background technique [0002] Organic semiconductor materials have attracted extensive attention due to their potential applications in organic electronic devices such as organic light-emitting diodes, organic field-effect transistors, and organic solar cells. The unique solution processability of organic semiconductor materials makes them extremely competitive with traditional inorganic semiconductor materials in the low-cost large-area production technology of future flexible electronics. In order to quickly push the field of organic electronics to commercial applications, more organic semiconductor materials with excellent performance need to be developed urgently. In the process of designing organic semiconductor materia...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 黄飞刘春晨曹镛
Owner SOUTH CHINA UNIV OF TECH
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