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A kind of organic polymer, its preparation method and application

A polymer and organic technology, applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve problems such as limiting industrial application and promotion, device manufacturing process and stability, and achieve good environmental stability and optoelectronics properties, favorable charge transport, and good solution processing properties

Active Publication Date: 2018-04-24
SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, at present, when polymer materials are made into thin film transistors, they are usually sensitive to environmental factors such as water and oxygen, which have a great impact on the manufacturing process and stability of the device, which will greatly limit its industrial application and promotion.

Method used

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  • A kind of organic polymer, its preparation method and application
  • A kind of organic polymer, its preparation method and application
  • A kind of organic polymer, its preparation method and application

Examples

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preparation example Construction

[0049] Such as figure 1 As shown, the preparation method of the aforementioned organic polymer includes: S10, halogenating the benzopyranochromene condensed with dithiophene to obtain its halogenated derivative; S20, combining the halogenated derivative with an aromatic group Ar The monomer is subjected to a coupling reaction under a metal catalyst to obtain the organic polymer. Wherein, after the coupling reaction, the aromatic group Ar is connected with the dithiophene-fused benzopyranochromene unit through conjugation.

[0050] Wherein, the synthesis of dithiophene-fused benzopyranochromene can refer to Chinese patent publication CN103497758A, the entire disclosure content of which is incorporated herein by reference. The foregoing coupling reactions include, but are not limited to, Suzuki coupling, Stille coupling, Negishi coupling, Hiyama coupling, C-H activated direct coupling, and the like.

[0051] As one of the schemes that can be implemented, the method includes bu...

Embodiment 1

[0056] The preparation of the organic polymer provided in this example mainly includes two parts: the preparation of the monomer and the polymerization reaction. First, the synthesis of dithiophene-fused benzopyranochromene can be prepared with reference to Chinese patent publication No. 103497758A, 2,7-bis(4,4,5,5-tetramethyl-1,3 , 2-dioxaborinane-diyl)-N-9-heptadecylcarbazole according to literature (N.Blouin, A.Michaud, M.Leclerc, Adv.Mater., 2007,19,2295-2300 )preparation.

[0057] Specifically, monomer 1 (dithiophene-fused benzopyranochromene) and polymer P 1 The synthetic route of (target product) is as follows:

[0058]

[0059]

[0060] 1. Synthesis of monomer 1:

[0061] Concrete reaction condition is: (1) Br 2 , CS 2 , reflux, 24h. (II)CH 3 COOH, Zn, reflux, 2h. (Ⅲ)C 8 h 17 MgBr, [NiCl 2 (dppp)], Et 2 O, reflux, 12h. (Ⅳ)Br 2 , CH 2 Cl 2 , rt, 2h.

[0062] More specifically:

[0063] Step (I): In the carbon disulfide solution (40mL) of benzopyr...

Embodiment 2

[0070] The synthetic route of the organic polymer in the present embodiment is as follows:

[0071]

[0072] One, the synthesis of monomer 1 is the same as in Example 1, another monomer 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)- Behenyl fluorene can be purchased directly.

[0073] 2. Polymer P 2 Synthesis:

[0074] 377mg (0.5mmol) 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-dioctylfluorene, 350mg (0.5mmol ) monomer 1,6mgPd 2 (dba) 3 , 12mg of P(o-tol) 3 Add it to a 25m1 two-necked bottle, pump and change gas three times until the hydrogen is full, add 4m120% Et with a syringe 4 NOHI organic base solution and 10mL toluene, reflux reaction for 72 hours, add phenylboronic acid and bromobenzene to block respectively, drop the reaction solution into methanol to precipitate polymer, then wash the polymer in a Soxhlet extractor, and finally remove the polymer After drying in a vacuum oven, finally obtain 245mg black polymer P 2 , Yield: 47%.

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Abstract

The invention discloses a novel organic polymer, its preparation method and application. The new organic polymer can be prepared by firstly halogenating the halogenated derivatives obtained by halogenating dithiophene-fused benzopyranochromene, and then reacting with monomers containing aromatic groups under a metal catalyst. The benzopyranochromene unit fused with the dithiophene is connected by conjugation. The novel organic polymer of the present invention has good environmental stability and photoelectric performance, and also has good solution processing performance, flexible synthesis, and easy subsequent modification treatment, and can be used in organic light-emitting diodes, organic thin film transistors and organic light sensors, etc. Widely used in various semiconductor electronics and optoelectronic devices.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a conjugated polymer organic semiconductor material, its preparation method and its application in the technical field of organic photoelectric materials. Background technique [0002] In recent years, the field of organic printed electronics, as an emerging and still developing field, has received extensive attention and rapid development in the past ten years. Organic electronic materials have the characteristics of rich variety, cheap raw materials, adjustable molecular properties through chemical composition modification, light, thin, and flexible products, especially the material can be processed by solution and can be printed, so that the roll-to-roll large area of ​​electronic devices can be realized. , low-cost manufacturing and has attracted much attention from the industry. Due to its simple printing process and non-selectivity to su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/54H01L51/46H01L51/30
CPCY02E10/549
Inventor 周春山崔铮
Owner SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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