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Naphthalimide derivant containing 1, 3-dithiol-2-yliden conjugation unit, preparation method and application

A technology of naphthalene diimide and derivatives is applied in the field of naphthalene diimide organic semiconductor materials, which can solve the problems of restricting the development of flexible electronic functional devices and shortage of n-type organic semiconductor materials with electron mobility.

Active Publication Date: 2013-11-27
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of n-type organic semiconductor materials is far behind that of p-type organic semiconductor materials, and there is an extreme shortage of high electron mobility, stable, and solution-processable n-type organic semiconductor materials, which greatly limits the development of organic complementary circuits. Development of flexible electronic functional devices (Anthony, J.E.; et al. Adv. Mater. 2010, 22, 3876)

Method used

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  • Naphthalimide derivant containing 1, 3-dithiol-2-yliden conjugation unit, preparation method and application
  • Naphthalimide derivant containing 1, 3-dithiol-2-yliden conjugation unit, preparation method and application
  • Naphthalimide derivant containing 1, 3-dithiol-2-yliden conjugation unit, preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0059] Example 1: N-(2-octyl-dodecyl)-N′-(4-tert-butylbenzyl)-[2,3-d:6,7-d′]-bis[2- Synthesis of (1,3-dithio-2-ylidene)-2-propanedicyano]-naphthalene-1,4,5,8-tetracarboxylic acid diimide (1).

[0060] Concrete synthetic steps are:

[0061] Under nitrogen protection, 2,3,6,7-tetrabromonaphthalene tetracarboxylic dianhydride (TBNDA) (300mg, 0.51mmol) and 1,1-dicyanoethylene-2,2-dithiolate sodium (288mg , 1.54mmol) was added to 50mL DMF and heated to 50°C. After stirring for 1 h, 2-octyl-dodecylamine (228 mg, 0.77 mmol) and 4-tert-butylbenzylamine (125 mg, 0.77 mmol) were added, and the reaction was continued at 50° C. for 5 h. Cool to room temperature, pour the reaction solution into 100mL saturated ammonium chloride solution, filter, wash the filter residue with water, dry in vacuo, use dichloromethane / petroleum ether (2:1) as eluent, and use a silica gel column to analyze the crude The product was separated and purified to obtain 50 mg of compound 1 as a brown-red solid wit...

Embodiment 2

[0064] Example 2: N-(2-octyl-dodecyl)-N′-(2,2-diphenyl-ethyl)-[2,3-d:6,7-d′]-bis Synthesis of [2-(1,3-dithio-2-ylidene)-2-propanedicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (2).

[0065] Concrete synthetic steps are:

[0066] Using 2,2-diphenylethylamine instead of p-tert-butylbenzylamine, the synthesis method was the same as that in Example 1, and a red solid (2) was prepared with a yield of 7%.

[0067] Mass Spectrum: [MS(TOF)]m / z:1003.3(M + ); H NMR spectrum: 1 H-NMR (300MHz, CDCl 3 )δ(ppm):0.839–0.891(m,6H,–CH 3 ),1.236–1.375(m,32H,–CH 2 –), 1.932-2.015 (b, 1H, –CH-), 4.191–4.216 (d, 2H, –CH 2 –),4.780–4.834(t,1H,–CH–),4.952-4.981(d,2H,–CH 2 –), 7.162–7.372 (m, 10H, Ph-H), 7.542-7.569 (d, 2H, Ph-H); elemental analysis calculated value (Anal.Calcd.For) C 56 h 54 N 6 o 4 S 4 :C,67.04;H,5.42;N,8.38;Found:C,67.32;H,5.64;N,8.51.

[0068]

Embodiment 3

[0069] Example 3: N,N'-bis(2-octyl-dodecyl)-[2,3-d]-[2-(1,3-dithio-2-ylidene)-2-propane Dicyano]-[6,7-d′][1,4-dithiacyclohexene-2,3-dinitrile]-naphthalene-1,4,5,8-tetracarboxylic diimide (3 )Synthesis.

[0070] Concrete synthetic steps are:

[0071] Under nitrogen protection, N,N'-bis(2-octyl-dodecyl)-2,3,6,7-tetrabromonaphthalene diimide (TBNDI-C20) (500mg, 0.44mmol) , 1,1-dicyanoethylene-2,2-sodium dithiolate (122mg, 0.66mmol) and 1,2-dicyanoethylene-1,2-sodium dithiolate (150mg, 0.79mmol) were added to In 100mL THF, stirred and reacted at -10°C for 2.5h, cooled to room temperature, poured the reaction solution into 200mL water, dissolved 4×100mL dichloromethane solution for extraction, combined the organic phases, dried, and spun off the solvent under reduced pressure. The crude product was purified by silica gel chromatography (eluent: dichloromethane / petroleum ether, V / V=1 / 1) to obtain 182 mg of compound 3 as a red solid with a yield of 38%.

[0072] Mass Spectrum: MS...

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Abstract

The invention relates to a naphthalimide derivant containing 1, 3-dithiol-2-yliden conjugation units, a preparation method and application thereof. The chemical structure is shown in the specification, wherein when Pi-1 or Pi-2 is groups shown in the specification, R<1> or R<2> is a C1-30 alkyl (of which the formula is shown in the specification), and R<3> is H or alkyls of C1-4; when Pi-1 is equal to Pi-2 and further shown in the specification, the R<1> and the R<2> can not be alkyls at the same time; when the R<1> is equal to the R<2>, both the R<1> and the R<2> are alkyls. All variants of the derivant can be an n-type organic semi-conductor material when the derivant is used to prepare organic thin film transistor devices, and tests show that the electron mobility in the air can reach 0.2cm<2>V<-1>s<-1>.

Description

technical field [0001] The invention relates to naphthalene diimide organic semiconductor materials containing 1,3-dithio-2-ylidene conjugated units, in particular to naphthalene containing 1,3-dithio-2-ylidene conjugated units Diimide derivatives, preparation methods and applications as n-type organic semiconductor materials in organic thin film field effect transistors. Background technique [0002] An organic thin film transistor (OTFT) is an active device that controls the conductivity of a solid organic semiconductor material through an electric field, and is one of the most basic unit devices in organic electronics. OTFT devices consist of electrodes (source / drain / gate), insulating layers and organic semiconductor layers; key parameters characterizing the performance of OTFT devices include: carrier mobility (μ, in cm 2 V -1 the s -1 ), on-off ratio (I on / I off ) and threshold voltage (V T , the unit is V). OTFT has the advantages of simple preparation process,...

Claims

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Application Information

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IPC IPC(8): C07D495/22H01L51/30
Inventor 高希珂胡云宾元伟朱道本
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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