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Tetracene derivative field effect transistor material and preparation method thereof

A technology of field effect transistors and derivatives, which is applied in the field of naphthacene derivatives field effect transistor materials and its preparation, can solve the problem of material stability reduction, unfavorable overlap of dry π conjugated orbitals, difficulty in achieving device mobility, etc. problem, to achieve the effect of improving stability, facilitating orderly accumulation of molecules, and easy separation

Active Publication Date: 2012-09-12
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example: pentacene is insoluble in most common organic solvents, so pentacene can only be used to prepare OFETs devices by physical vapor deposition; it has a relatively low highest occupied orbital (HOMO) energy level, and is prone to oxidation or free radicals The stability of the material is reduced due to the reaction; the condensed state presents a "fishbone-like" face-to-edge (Herringbone) arrangement, which is not conducive to the overlapping of dry π-conjugated orbitals, which makes it difficult for the mobility of the device to reach the material itself. reached the limit

Method used

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  • Tetracene derivative field effect transistor material and preparation method thereof
  • Tetracene derivative field effect transistor material and preparation method thereof
  • Tetracene derivative field effect transistor material and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0026] In a single-necked round-bottom flask (250 mL), add pyrene (10 g, 49.5 mmol), anhydrous aluminum trichloride (0.65 g, 4.92 mmol) and dichloromethane (100 mL), under nitrogen protection, and stir at room temperature. Then, tert-butyl chloride (10.05 g, 108.4 mmol) was dissolved in dichloromethane solution (15 mL), and slowly added to the reaction system. After the dropwise addition was completed, stirring was continued at room temperature for 6 h. Neutralize the aluminum chloride in the reaction system with glacial hydrochloric acid (3 M), extract with dichloromethane, wash the organic phase with water, saturated sodium bicarbonate, and saturated sodium chloride solution, dry over anhydrous magnesium sulfate, concentrate, and recrystallize from ethanol 9 g of 2, 7-di-tert-butylpyrene was obtained with a yield of 57.5%. 1 H NMR (400 MHz, CDCl 3 )δ (ppm): 8.18(s, 4H), 8.02(s, 4H), 1.58(s, 18H).

[0027] Add 2,7-di-tert-butylpyrene (7.32 g, 20 mmol), iron powder (2.5 g, ...

Embodiment 2

[0034] Add Pd(PPh 3 ) 4 (1.2 g, 1 mmol) and CuI (189 mg, 1 mmol), 1,4-dimethyl-4-bromobenzene (7.4 g, 40 mmol) and trimethylsilylacetylene (4.32 mg , 44 mmol) of diisopropylamine and tetrahydrofuran mixed solution (150 mL, v / v=1 / 1), dropwise, 80 o C for 12 h. Cool, filter, concentrate the filtrate, and separate and purify by silica gel column to obtain 5 g of 1,2-dimethyl-4-trimethylsilylethynylbenzene with a yield of 61.9%. 1 H NMR (400 MHz, CDCl 3 )δ(ppm): 7.26(s, 1H), 7.20-7.22(d, 1H), 7.05-7.07(d, 1H), 2.23-2.25(t, 3H), 0.25(s, 9H).

[0035] Add 1,2-dimethyl-4-trimethylsilylethynylbenzene (5 g, 25 mmol), KOH (6.72 g, 120 mmol) and methanol (300 mL) into a one-necked bottle (500 mL), 80 o C was reacted for 1 h, cooled, extracted with dichloromethane, concentrated, and purified by silica gel column chromatography to obtain 2.4 g of 1,2-dimethyl-4-ethynylbenzene with a yield of 74.5%. 1 H NMR (400 MHz, CDCl 3 )δ(ppm): 7.29(s, 1H), 7.23-7.26(d, 1H), 7.08-7.09(d, 1H), 3....

Embodiment 3

[0039] Add 1, 2-dioctyloxybenzene (6.68 g, 20 mmol) and acetic acid (100 mL) into a two-neck flask (250 mL), stir to dissolve, and add N-bromosuccinimide (NBS ) (3.6 g, 20 mmol), reacted at room temperature for 1 h, then added NBS (0.5 g), and reacted at room temperature for 1 h. After the reaction, use NaHCO 3 Adjust the pH of the aqueous solution to neutral, extract with dichloromethane, concentrate, and recrystallize from acetone to obtain 7 g of 1,2-dioctyloxy-4-bromobenzene, with a yield of 84.6%. 1 H NMR (400 MHz, CDCl 3 )δ(ppm): 6.97-6.99(d, 1H), 6.97(s, 1H), 6.72-6.74(d, 1H), 3.94-3.96(t, 4H), 1.77-1.82(m, 4H), 1.45 (s, 4H),1.28-1.30(d,16H), 0.87-0.88(t, 6H).

[0040] Add 1,4-dioctyloxy-4-bromobenzene (4.13 g, 10 mmol), Pd(PPh 3 ) 4 (300 mg, 0.25 mmol) and CuI (48 mg, 0.25 mmol), added dropwise trimethylsilylacetylene (4.32 mg, 44 mmol) in diisopropylamine and tetrahydrofuran mixed solution (40 mL, v / v= 1 / 1), the addition is complete, 80 o C stirred for 12 h. C...

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Abstract

The invention discloses a tetracene derivative field effect transistor material and a preparation method thereof. The tetracene derivative field effect transistor material has a general structural formula I, wherein Ar represents aryl, substituted aryl, heterocyclic aryl or substituted heterocyclic aryl and R represents one of alkyl, alkoxy, alkyl sulphanyl and the like. The tetracene derivative field effect transistor material can be synthesized by a Sonogashira coupling reaction and a Bergman cyclization reaction. The tetracene derivative field effect transistor material has high stability and high dissolvability and can improve a mobility ratio of OFETs devices.

Description

technical field [0001] The invention relates to a class of condensed ring conjugated materials, specifically a class of naphthacene derivative field effect transistor materials and a preparation method thereof. Background technique [0002] Organic semiconductor materials have the advantages of strong structure flexibility, solution processing and flexible substrates, and become the main body of the new generation of electronic information materials. The research and development of new and efficient organic conjugated semiconductor materials will have broad market prospects in the electronics industry. Among them, linear acene materials (Acenes) are particularly attractive. Acene materials 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 / 2D Fusedaceneorheteroacene) materials have shown extremely high device mobility. For example, Pentacene (Pentacene), rub...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/08C07C15/20C07C2/88C07C43/205C07C41/30C07D333/18
Inventor 田波黄维傅妮娜赵保敏黄红艳
Owner NANJING UNIV OF POSTS & TELECOMM
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