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Heterocyclic-sulfur fused naphthalene diimide compounds, preparation method and application thereof

A naphthalene diimide and compound technology, which is applied in the field of bis[2-malononitrile] fused naphthalene diimide compounds, can solve the problem of single types of n-type organic semiconductor materials, etc.

Inactive Publication Date: 2012-02-15
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the NDI-DTYM2 series n-type organic semiconductor materials disclosed in the previous patents (CN200910197611.9, PCT / CN2010 / 077932) are relatively single in type, and the N-substituents are limited to alkyl groups, most of which are "dovetail type" long-branched N -Alkyl; and the example compounds disclosed are mostly symmetrical N-substituted derivatives

Method used

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  • Heterocyclic-sulfur fused naphthalene diimide compounds, preparation method and application thereof
  • Heterocyclic-sulfur fused naphthalene diimide compounds, preparation method and application thereof
  • Heterocyclic-sulfur fused naphthalene diimide compounds, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Example 1: N, N'-bis(2,2-bis(octyloxy)-1-ethyl)-[2,3-d:6,7-d']-bis[2-(1, Synthesis of 3-dithiacyclopentene-2-ylidene)-2-propanedicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (1).

[0110]

[0111] Under nitrogen protection, 2,3,6,7-tetrabromonaphthalene tetracarboxylic dianhydride (TBNDA) (100mg, 0.17mmol) and 1,1-dicyanoethylene-2,2-dithiolate sodium (96mg , 0.52mmol) was added into 15mL DMF and heated to 50°C. After stirring for 1 h, 2,2-bis(octyloxy)ethylamine (207 mg, 0.68 mmol) was added, and the temperature was maintained for 7 h. Cool to room temperature, pour the reaction solution into 100 mL of 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 chromatography column to analyze the crude The product was separated and purified to obtain compound 1 as a brown-red solid with a yield of 42%. Mass spectrum: MS (EI) m / z 1110.8 (M + ); H N...

Embodiment 2

[0112] Example 2: N, N'-bis(4-tert-butylphenyl)-[2,3-d:6,7-d']-bis[2-(1,3-dithiecyclopentene- Synthesis of 2-ylidene)-2-propanedicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (2).

[0113]

[0114] Using 4-tert-butylaniline instead of 2,2-bis(octyloxy)-ethyl-1-amine, the synthesis method was the same as in Example 1 to obtain compound 2 as a dark red solid with a yield of 55%. Mass Spectrum: MS (MALDI-TOF) m / z 807.1 (M + ); H NMR spectrum: 1 H-NMR (300MHz, CDCl 3 )δ (ppm): 1.415 (s, 9H, -CH 3 ), 7.291-7.318 (d, 2H, H-Ph), 7.666-7.694 (d, 2H, H-Ph); elemental analysis calculated value (Anal. Calcd. For) C 42 h 26 N 6 o 4 S 4 : C, 62.51; H, 3.25; N, 10.41; Found: C, 62.49; H, 3.27; N, 10.54.

Embodiment 3

[0115] Example 3: N, N'-bis(3,4,5-tri(dodecyloxy)phenyl)-[2,3-d:6,7-d']-bis[2-(1 , Synthesis of 3-dithiacyclopentene-2-ylidene)-2-propanedicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (3).

[0116]

[0117] Replace 2,2-bis(octyloxy)-ethyl-1-amine with 3,4,5-tris(dodecyloxy)aniline, and the synthesis method is the same as in Example 1 to obtain 128 mg of blue-purple solid 3, producing rate 42%. Mass Spectrum: MS (MALDI-TOF) m / z 1799.3 (M + ); H NMR spectrum:1 H-NMR (300MHz, CDCl 3 )δ (ppm): 0.851-0.895 (m, 9H, -CH 3 ), 1.256-1.276 (m, 53H, -CH 2 -), 1.442-1.482(m, 6H), 1.775-1.844(m, 6H), 3.944-4.072(t, 6H, -CH 2 -O), 6.501 (s, 2H, H-Ph); C NMR spectrum: 13 C-NMR (100Hz, CDCl 3 ):δ14.104,14.115,22.653,22.680,22.701,22.719,26.096,26.132,29.310,29.360,29.401,29.416,29.638,29.656,29.705,29.714,29.769,29.779,29.787,30.406,31.918,31.925,31.948, 32.770, 69.367, 71.772, 73.738, 106.102, 111.309, 118.060, 125.450, 127.295, 139.539, 145.858, 154.182, 161.941, 181.278 (C...

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Abstract

The invention relates to bis[2-(1, 3-dithiocyclopenta-2-ylidene) malononitrile] fused naphthalene diimide compounds, a preparation method and application thereof. The compounds have a structure as shown in the following formula. Tetrabromothalene dianhydride, and 2, 2-dicyano-ethene-1, 1-dithiolate, as well as organic amine are subjected to a reaction in an organic solvent, so as to prepare the bis[2-(1, 3-dithiocyclopenta-2-ylidene) malononitrile] fused naphthalene diimide compounds by a one pot process. The compounds can be symmetrical N- substituted and asymmetrical N- substituted compounds. The compounds can be adopted as an n-type organic semiconductor material, and a transistor of a solution cast film made of this material has mobility up to 0.65cm<2> / Vs. Also with good environmental stability, the compounds have extensive application prospects in the field of organic electronics.

Description

technical field [0001] The present invention relates to sulfur heterocyclic fused naphthalene diimide organic semiconductor materials, in particular to bis[2-(1,3-dithiecyclopentene-2-ylidene) malononitrile] fused Naphthalene diimide compound, preparation method and application as n-type organic semiconductor material in organic thin film field effect transistor and the like. Background technique [0002] Organic thin film transistors (OTFT) have the advantages of simple preparation process, low cost, light weight, flexibility, and good compatibility with plastic substrates. It is used in smart cards, electronic tags, electronic paper, active matrix Display, sensor, memory and other flexible electronic products have broad application prospects (Nature 2004, 428, 911-918.; Science 2009, 326, 1516-1519.; Nat.Mater.2010, 9, 859-864.; Adv . Mater. 2010, 22, 3778-3798.; Science 2010, 327, 1603-1607). According to the latest forecast by the British AIM, by 2029, the total sales ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22H01L51/30
Inventor 高希珂狄重安胡云宾朱道本秦云科
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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