Thia-conjugated compound taking naphthalene tetracarboxylic acid diimide as kernel as well as preparation method and application thereof

A technology of naphthalene tetracarboxylic acid diimide and conjugated compounds, which is applied in the field of n-type organic semiconductor materials, can solve the problems of low electron mobility, difficulty in forming, and poor film-forming properties of OTFT devices, and achieve a simple and effective synthesis method , high purity, excellent performance and stability

Active Publication Date: 2010-04-14
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

However, its small conjugated aromatic ring makes it difficult to form effective π-π stacking in solid structures, and its OTFT devices have low electron

Method used

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  • Thia-conjugated compound taking naphthalene tetracarboxylic acid diimide as kernel as well as preparation method and application thereof
  • Thia-conjugated compound taking naphthalene tetracarboxylic acid diimide as kernel as well as preparation method and application thereof
  • Thia-conjugated compound taking naphthalene tetracarboxylic acid diimide as kernel as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: N,N'-Dioctyl-[2,3-d:6,7-d']-bis[1,3-Dithia-2-yeryne-propanedicyano]-naphthalene - Synthesis of 1,4,5,8-tetracarboxylic diimide (1).

[0042] Concrete synthetic steps are:

[0043] 1.1 Synthesis of 2,3,6,7-tetrabromonaphthalene tetracarboxylic dianhydride (TBNDA)

[0044] 450mL 20% oleum was mixed into a 1L three-necked flask, and naphthalenetetracarboxylic dianhydride (NDA) (16g, 59.7mmol), liquid bromine (16mL, 320mmol) and 0.8g iodine (catalyst) were added thereto. Raise the temperature of the reaction mixture to 130°C, heat the reaction for 78 hours, then lower it to room temperature, remove unreacted liquid bromine with nitrogen flow, pour the reaction solution into 1Kg of crushed ice, filter, and wash the precipitate with a large amount of water until the filtrate is neutral. Drying in vacuo yielded 28 g of a yellow powdery solid (TBNDA), with a yield of 81%.

[0045] Mass Spectrum (MS-EI)) m / z 584 (M + , 95%)

[0046] 1.2 Synthesis of N,N'-dioctyl...

Embodiment 2

[0059] Example 2: N, N'-bis(2-ethyl-hexyl)-[2,3-d:6,7-d']-bis[1,3-dithia-2-yrylene- Synthesis of malondicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (2).

[0060] Concrete synthetic steps are:

[0061] 2.1 Synthesis of N, N'-bis(2-ethyl-hexyl)-2,3,6,7-tetrabromo-naphthalene tetracarboxylic acid diimide

[0062] Using 2-ethyl-hexylamine instead of n-octylamine, the synthesis method is the same as step 1.2 in Example 1, and the yield is 33%.

[0063] Mass Spectrum: [MS(TOF)]m / z: 806.8(M + ), 884.3(M+2K) + .

[0064] H NMR spectrum: 1 H-NMR (300MHz, CDCl 3 )δ (ppm): 0.859-0.969 (m, 6H), 1.287-1.409 (m, 8H), 1.923-1.967 (m, 1H), 4.169-4.194 (d, J=7.50Hz, 2H).

[0065] 2.2 Synthesis of example compound 2

[0066] Replace N, N'- Dioctyl-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide, synthetic method is with step 1.4 in the embodiment 1, prepares dark brown solid (2 ), yield 51%.

[0067] Mass Spectrum: [MS(TOF)]m / z: 767.5(M + ).

[0068] Elemental ...

Embodiment 3

[0070] Example 3: N, N'-bis(2-octyl-dodecyl)-[2,3-d:6,7-d']-bis[1,3-dithia-2-phyllo Synthesis of orylene-propanedicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (3).

[0071] Concrete synthetic steps are:

[0072] 3.1. Synthesis of N,N'-bis(2-octyl-dodecyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide

[0073] Using 2-octyl-dodecylamine instead of n-octylamine, the synthesis method is the same as step 1.2 in Example 1, and the yield is 33%.

[0074] Mass spectrum: [MS(TOF)] m / z: 1144.8 (M + ).

[0075] H NMR spectrum: 1 H-NMR (300MHz, CDCl 3 )δ (ppm): 0.863-0.888 (m, 6H), 1.235 (b, 32H), 1.966-2.008 (m, 1H), 4.159-4.183 (d, J=7.20Hz, 2H).

[0076] 3.2 Synthesis of example compound 3

[0077] Replace N with N,N'-bis(2-octyl-dodecyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide, N'-dioctyl-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic diimide, the synthetic method is the same as step 1.4 in Example 1, and reddish brown is obt...

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Abstract

The invention relates to a thia-conjugated compound taking naphthalene tetracarboxylic acid diimide as a kernel as well as a preparation method and application thereof. The structure of the thia-conjugated compound is shown as the follow formula; in the formula, R is C1-C30 of n-alkyl or branch alkyl. Under the protection of inert gas, 2,3,6,7-tetrabromoaphthalene tetracarboxylic acid diimide reacts with 1,1-dicyano-2,2-dithiolate disodium salt in tetrahydrofuran respectively at room temperature and the temperature of 40-60 DEG C for 0.5-2 hours and 0.5-1 hour, a silicagel column is subjected to chromatography to obtain a target compound, and the production ratio is 50-62 percent; an organic thinner film field effect transistor prepared by a solution method and taking the compound as an organic semiconductor layer achieves highest electronic mobility up to 0.15 cm2/Vs, switch ratio of larger than 107 and threshold voltage of lower than 15V, and the performance and environment stability thereof are superior to those of common n-shaped organic semiconductors.

Description

technical field [0001] The present invention relates to a kind of n-type organic semiconductor material that can be formed into film by solution method, in particular to a class of thia conjugated compound with naphthalene tetracarboxylic acid diimide as the core, its preparation method and its use as an organic semiconductor material in Applications in Organic Thin Film Field Effect Transistors. Background technique [0002] Organic thin film transistors (OTFT for short) are active devices that control the conductivity of organic semiconductor materials through an electric field. OTFT has the advantages of simple preparation process, low cost, light weight, flexibility, and good compatibility with plastic substrates. It has broad application prospects in flexible displays, organic radio frequency electronic labels (ORFID), organic sensors, etc. (Forrest , S.R.Nature.2004, 428, 911-918; Korzhov, M.et al.Physics Word.2008, 29-33; Leenen, M.A.M.et al.Phys.Status Solidi A.2009...

Claims

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Application Information

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IPC IPC(8): C07D495/22H01L51/05H01L51/10H01L51/30H01L51/40
Inventor 高希珂狄重安朱道本刘云圻李洪祥姜标
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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