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Organic semiconductor material containing naphthalene tetracarboxylic acid diimide, its preparation method and application

A technology containing naphthalene tetracarboxylic acid diimide and naphthalene tetracarboxylic acid diimide, which is applied in semiconductor/solid-state device manufacturing, semiconductor devices, light-emitting materials, etc., can solve the problem of low collection efficiency of carrier electrodes, red The light area is not effectively utilized, low carrier mobility, etc., to achieve the effect of reducing charge transfer complexes, improving transport properties, and increasing carrier mobility

Inactive Publication Date: 2012-02-08
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the research on polymer solar cells mainly focuses on the blending system of donor and acceptor, using PTB7 and PC 71 The energy conversion efficiency of the BM blend system has reached 7.4%, but it is still much lower than the conversion efficiency of inorganic solar cells. The main constraints that limit the performance improvement are: the relatively low carrier mobility of organic semiconductor devices, the device’s The spectral response does not match the solar radiation spectrum, the red light region with high photon flux is not effectively utilized, and the electrode collection efficiency of carriers is low, etc.

Method used

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  • Organic semiconductor material containing naphthalene tetracarboxylic acid diimide, its preparation method and application
  • Organic semiconductor material containing naphthalene tetracarboxylic acid diimide, its preparation method and application
  • Organic semiconductor material containing naphthalene tetracarboxylic acid diimide, its preparation method and application

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preparation example Construction

[0032] This embodiment also provides a method for preparing the above-mentioned organic semiconductor material containing diimide units of naphthalene tetracarboxylic acid, including the following steps:

[0033] S11. Compounds A, B, and C represented by the following structural formula are provided respectively,

[0034] Among them; R 1 from C 1 ~C 20 the alkyl group; R 2 from C 1 ~C 20 Alkyl, phenyl or C 1 ~C 20 alkoxy;

[0035] S12. In an oxygen-free environment and under the condition that catalyzer and the first organic solvent exist, select compound A, B, C to carry out Stille coupling reaction, obtain following structural general formula and be the diimide containing naphthalene tetracarboxylic acid represented by (I) Amine unit organic semiconductor materials,

[0036]

[0037] In the general structural formula (I), x+y=2; 1≤x, 0<y<1; n is an integer, and 1<n≤100. The Stille coupling reaction formula in its preparation method is:

[0038]

[0039] In...

Embodiment 1

[0061] Preparation of Dithiophene[3,2-b:2',3'-d]silole-N,N'-Dialkyl Substituted-1,4,5,8-Naphthalene Tetracarboxylic Diimide Organic Semiconductor , its structural formula is as follows I 1 as shown,

[0062]

[0063] Its preparation steps are as follows:

[0064] 1) N, the preparation of N'-dioctyl-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide, its chemical reaction formula is as follows:

[0065]

[0066] The specific process of preparation is: under the protection of nitrogen, n-octylamine (0.13g, 1mmol) is added to the propane containing 2,6-dibromo-1,4,5,8-naphthalene dianhydride (0.43g, 0.1mmol0). acid (15mL) solution, refluxed for 12 hours, cooled to room temperature, the reaction solution was poured into an aqueous sodium hydroxide solution, extracted with chloroform, removed the organic solvent, washed with ethyl acetate, dissolved in chloroform, and then column chromatography (alumina chromatographic column ), remove solvent to obtain solid pro...

Embodiment 2

[0074] Preparation of Dithiophene[3,2-b:2',3'-d]silole-N,N'-Dialkyl Substituted-1,4,5,8-Naphthalene Tetracarboxylic Diimide Organic Semiconductor , its structural formula is as follows I 2 as shown,

[0075]

[0076] Its preparation steps are as follows:

[0077] 1) According to the same preparation method and similar reaction conditions in step 1) in Example 1, the compound N, N'-di-(n-eicosyl)-2,6-dibromo-1,4 with the following structural formula was prepared , 5,8-naphthalene tetracarboxylic diimide,

[0078]

[0079] 2) According to the same preparation method and similar reaction conditions as step 2) in Example 1, 4,4-dioctyl-2,6-bistrimethyltin-dithiophene[3,2-b with the following structural formula was prepared :2',3'-d]silole,

[0080]

[0081] 3) Dithiophene[3,2-b:2',3'-d]silole-N,N'-dialkyl substituted-1,4,5,8-naphthalene tetracarboxylic acid diimide organic semiconductor I 2 The synthesis, its chemical reaction formula is as follows:

[0082]

[...

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Abstract

The invention discloses an organic semiconductor material containing naphthalene tetracarboxylic acid diimide, its preparation method and application. The material is represented as the formula (I), wherein, x+y=2, x is no less than 1, y is larger than 0 and less than 1, n represents an interger which is larger than 1 and no larger than 100, R1 is selected from C1-C20 alkyl, and R2 is selected from C1-C20 alkyl, phenyl or C1-C20 alkyloxy. The organic semiconductor material is prepared by polymerization of dithieno [3, 2-b: 2', 3'-d] silole and naphthalene tetracarboxylic acid diimide. According to the invention, the crystallization performance of the organic semiconductor material is improved, the double molecular composite reaction is weakened, the carrier mobility is increased, and the spectral response is broadened. The organic semiconductor material has good hole-transmission properties, and electrochemical reduction properties, and according to the invention, the solubility can be improved by introducing alkyl chains with simple methods.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to an organic semiconductor material containing naphthalene tetracarboxylic diimide unit and its preparation method and application. Background technique [0002] The preparation of low-cost and high-efficiency solar cells using cheap materials has always been a research hotspot and difficulty in the field of photovoltaics. Silicon solar cells currently used on the ground are limited in application due to complex production processes and high costs. In order to reduce the cost and expand the scope of application, people have been looking for new solar cell materials for a long time. Polymer solar cells have attracted much attention due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating and printing. If the energy conversion efficiency can be improved to be close to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/46H01L51/54H01L51/30H01S5/36
CPCY02E10/549
Inventor 周明杰黄杰许二建
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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