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Amino/amine oxide modified perylene diimide derivative as well as preparation method and application thereof

A perylene diimide and derivative technology, applied in the field of organic optical devices, can solve the problems of low work function metal instability and unfavorable processing of organic semiconductor devices, etc., and achieve the effects of easy acquisition, high yield and simple synthesis method

Active Publication Date: 2014-02-05
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these low work function metals are unstable in the air and easily react with water and oxygen in the air
In addition, these metals need to be vacuum evaporated, which is not conducive to the realization of full solution processing of organic semiconductor devices, so people began to look for organic electronic buffer layer materials that can realize solution processing to replace low work function Ca. (H.-L.Yip, A.K.Y.Jen ,Energy Environ.Sci.2012,5,5994)

Method used

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  • Amino/amine oxide modified perylene diimide derivative as well as preparation method and application thereof
  • Amino/amine oxide modified perylene diimide derivative as well as preparation method and application thereof
  • Amino/amine oxide modified perylene diimide derivative as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Embodiment 1, the perylene diimide (that is, PDIN) of the amino group modification shown in the preparation formula III

[0078] Referring to the literature method (Angew Chem Int Ed2010, 49(8), 1485), under nitrogen atmosphere, pyrene tetraic anhydride (10 g, 25.6 mmol) and primary amine derivative N,N-dimethyl-1,3-di Aminopropane (equivalent to R in formula IX 1 for -ch 2 CH 2 CH 2 -,R 2 for -ch 3 ) (26.2 g, 141.6 mmol) in tert-butanol solution (500 mL), heated under reflux for 24 hours. Cooled to room temperature, the suspension was separated by filtration, and the filter cake was washed with ethanol and ether in turn. The product was obtained after drying. Yield 80%.

[0079] figure 1 The absorption spectrum of PDIN in a shows that there is a red shift in the absorption in the film compared to the solution, indicating that there is a strong intermolecular interaction between molecules in the solid state.

[0080] figure 1 The cyclic voltammogram of PDIN i...

Embodiment 2

[0085] Example 2. Preparation of amine group-modified perylene diimide shown in formula IV

[0086] With reference to the preparation method of formula III in Example 1, under nitrogen atmosphere, pyrene tetraic anhydride (10 g, 25.6 mmol) and primary amine derivative N,N-diethylethylenediamine (equivalent to formula IX, R 1 for -ch 2 CH 2 -,R 2 for -ch 2 CH 3 ) (16.45 g, 141.6 mmol) in tert-butanol solution (500 mL), heated under reflux for 24 hours. Cooled to room temperature, the suspension was separated by filtration, and the filter cake was washed with ethanol and ether in turn. The product was obtained after drying. Yield 80%.

[0087] The structural confirmation of this product is shown below: 1 H-NMR (400MHz, CF3COOD, δ, ppm): 8.90(4H), 8.95(4H), 4.89(4H), 3.80(4H), 3.60(8H), and 1.60(12H).

Embodiment 3

[0088] Example 3. Preparation of amine group-modified perylene diimide shown in formula V

[0089] Referring to the preparation method of formula III in Example 1, under nitrogen atmosphere, pyrene tetraic anhydride (10 g, 25.6 mmol) and primary amine derivative N,N-dimethylethylenediamine (equivalent to formula IX, R 1 for -ch 2 CH 2 -,R 2 for -ch 3 ) (20.0 g, 128.1 mmol) in tert-butanol solution (500 mL), heated under reflux for 24 hours. Cooled to room temperature, the suspension was separated by filtration, and the filter cake was washed with ethanol and ether in turn. The product was obtained after drying. Yield 80%.

[0090] The structural confirmation of this product is shown below: 1 H-NMR (400 MHz, CF3COOD, δ, ppm): 8.90 (4H), 8.95 (4H), 4.89 (4H), 3.80 (4H), 2.24 (6H).

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Abstract

The invention provides an amino / amine oxide modified perylene diimide derivative as well as a preparation method and application thereof. A structural general formula of the amino modified perylene diimide derivative is represented in formula I or formula II, wherein R1 is selected from C1-C10 alkylene; R2 is same to or different with the R1, is independently selected from H and C1-C10 alkyl; C4 represents substituted C1-C10 alkyl, wherein R4 is selected from hydroxyl, halogen and alkoxy; R3 same or different, is independently selected from H, OH, N(R5)2, Cl or Br; and R5, same or different, is selected from H or C1-6 alkyl. The synthesis route of the perylene diimide materials has advantages of being simple and efficient, low in environmental pollution, cheap in raw material, low in synthesis cost, excellent in universality and repeatability, and the like; and the amino / amine oxide polar group is free from negative ion, so that stability of a component is obviously improved.

Description

technical field [0001] The invention relates to an amine group / amine oxide modified perylene diimide derivative, a preparation method and application thereof. In particular, it relates to organic optical devices comprising said perylene diimide derivatives. Background technique [0002] In the field of organic semiconductors, in order to improve the injection or collection of electrons, metals with low work function such as Ca / Al are usually used as cathodes. However, these low work function metals are unstable in air and readily react with water and oxygen in air. In addition, these metals require vacuum evaporation, which is not conducive to the realization of full solution processing of organic semiconductor devices. Therefore, people began to look for organic electronic buffer layer materials that can realize solution processing to replace low work function Ca. (H.-L.Yip, A.K.Y.Jen , Energy Environ. Sci. 2012, 5, 5994). In addition, the outstanding advantage of organi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06H01L51/46H01L51/48H01L51/54
CPCY02E10/549C07D471/06H10K85/621Y02P70/50
Inventor 张志国王吉政靳志文李永舫
Owner INST OF CHEM CHINESE ACAD OF SCI
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