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2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer, preparation method of 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer and polymer

A pyrazine derivative, 10-technology, applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the problems of low polymer performance and difficulty in monomer synthesis, and improve molecular weight. , The effect of low raw material price and high photoelectric conversion efficiency

Active Publication Date: 2014-04-16
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims at the shortcomings of difficult monomer synthesis and low polymer performance in the prior art, and provides a new method for synthesizing a class of 2,7-alkyl substituted phenanthrene[9,10-b]pyrazine derivative monomers

Method used

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  • 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer, preparation method of 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer and polymer
  • 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer, preparation method of 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer and polymer
  • 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer, preparation method of 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer and polymer

Examples

Experimental program
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Effect test

Embodiment 1

[0033]Example 1: Preparation of 2,7-dioctyl-9,10-phenanthrenequinone

[0034] (1) The preparation of 2,7-dibromo-9,10-phenanthrenequinone is prepared according to the method disclosed in [Polym.Int.2007,56,1507.], and the reaction formula is as follows:

[0035]

[0036] In a 500ml three-neck round bottom flask, add 9,10-phenanthrenequinone (20.8g, 100mmol) and concentrated sulfuric acid (300ml), mechanically stir for 15 minutes, add bromosuccinimide (NBS) (40g, 220mmol ). The reaction was carried out in the dark for 24 hours. After the reaction was completed, the reactant was slowly poured into ice water, filtered with suction, and the filter residue was washed several times with aqueous sodium bicarbonate solution, water and methanol in sequence. After the filter residue was dried, it was recrystallized with N,N-dimethylformamide (DMF) to obtain 22 g of an orange solid, yield: 60%. (2) Preparation of 2,7-dibromo-9,10-dihydroxyphenanthrene, according to [Jpn.Kokai Tokkyo...

Embodiment 2

[0049] Example 2: Preparation of 10,13-dibromo-2,7-dioctyldibenzo[a,c]phenazine, the reaction formula is as follows:

[0050]

[0051] In a 50 ml three-necked flask, add 2,7-dioctyl-9,10-phenanthrenequinone (4.32g, 10mmol), 3,6-dibromo-1,2-phenylenediamine (2.66g, 10mmol), Acetic acid (20 mL) and tetrahydrofuran (5 mL) were heated and stirred at 60°C overnight. After the reaction was completed, the reactant was poured into water, filtered, and the filter residue was recrystallized from a mixed solution of ethanol / tetrahydrofuran to obtain 5.9 g of a light yellow solid, with a yield of 90%. 1 H NMR (300MHz, CDCl3) δ (ppm): 9.12 (s2H), 8.33 (d, 2H), 7.97 (s, 2H), 7.58 (d, 2H), 2.89 (t, 4H), 1.83-1.75 (m ,4H), 1.46-1.25(m,20H), 0.88(t,6H).

Embodiment 3

[0052] Example 3: Preparation of 10,13-dibromo-2,7-dioctyldibenzo[f,h]pyrido[4,3-b]quinoxaline, the reaction formula is as follows:

[0053]

[0054] In a 50 ml three-necked flask, add 2,7-dioctyl-9,10-phenanthrenequinone (2.16g, 5mmol), 3,4-diamino-2,5-dibromopyridine (1.34g, 5mmol), Acetic acid (20 mL) and tetrahydrofuran (5 mL) were heated and stirred at 60°C overnight. After the reaction was completed, the reactant was poured into water, filtered, and the filter residue was recrystallized from a mixed solution of ethanol / tetrahydrofuran to obtain 3 g of dark yellow solid, yield: 90%. 1 H NMR (300MHz, CDCl3) δ (ppm): 8.87 (s2H), 8.75 (s, 1H), 8.17 (d, 2H), 7.53 (t, 2H), 2.83 (t, 4H), 1.79-1.74 (m ,4H), 1.41-1.25(m,20H), 0.89(t,6H).

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Abstract

The invention relates to a 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer, a preparation method of the 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer, and a polymer. The 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer has a large pi conjugation rigid plane and stronger electron affinity. The introduction of 2,7-alkyl has a critical effect in improving performances, such as molecular weight, solubility, processibility or self-assembly, of the monomer or the relevant polymer. The 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer is synthesized by phenanthraquinone bromination, reduction, hydroxyl protection, 2,7-alkylation, fuming nitric acid oxidation deprotection, ring closing and the like, and is easy to synthesize and purify, raw materials are low in price, and the mass production is facilitated. A homopolymer or a copolymer can be obtained by Suzuki, Stille or Yamamoto polymerization reaction of the 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer. The series of polymers have good solubility in an organic solvent, are suitable for solution processing, and have wide application prospects in the fields of organic panel display, photovoltaic batteries, and organic field effect transistors.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, in particular to a preparation method and application of a class of 2,7-alkyl substituted phenanthrene[9,10-b]pyrazine derivative monomers and polymers thereof. Background technique [0002] With the aggravation of energy crisis, environmental pollution and other issues, the development and utilization of new energy is gradually advocated by people, and solar energy, as a sustainable renewable clean energy, has also become a hot spot in the development of new energy. The energy conversion efficiency of common silicon-based solar cell materials reaches more than 25%, which has reached the practical requirements and has been applied in aviation, military and civil fields. However, the production cost of monocrystalline silicon and amorphous silicon is too expensive, and this bottleneck prevents silicon-based solar cells from being widely used. Organic solar cells are a new type of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/36C07D471/04C07D409/14C08G61/12C09K11/06H01L51/00H01L51/46H01L51/54H01L51/30H10K99/00
CPCY02E10/549C07D241/38C07D409/14C07D471/04C08G61/122C08G61/126C08G2261/3243C08G2261/3241C08G2261/3223C08G2261/91H10K85/111H10K85/113Y02P70/50
Inventor 杨伟何锐锋张斌吴宏滨曹镛
Owner SOUTH CHINA UNIV OF TECH
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