2,7-Alkyl-substituted phenanthrene[9,10-b]pyrazine derivative monomer and its preparation method 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 difficult monomer synthesis and low polymer performance, and achieve the price of raw materials Low cost, increased molecular weight, high mobility effect

Active Publication Date: 2016-07-06
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 phenanthrene[9,10-b]pyrazine derivative monomer and its preparation method and polymer
  • 2,7-Alkyl-substituted phenanthrene[9,10-b]pyrazine derivative monomer and its preparation method and polymer
  • 2,7-Alkyl-substituted phenanthrene[9,10-b]pyrazine derivative monomer and its preparation method and polymer

Examples

Experimental program
Comparison scheme
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 orange solid, yield: 60%. (2) Preparation of 2,7-dibromo-9,10-dihydroxyphenanthrene, according to [Jpn.KokaiTokkyoKoho...

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 HNMR (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 HNMR (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 phenanthrene[9,10-b]pyrazine derivative monomer, a preparation method thereof and a polymer. The 2,7-alkyl-substituted phenanthrene[9,10-b]pyrazine derivative unit has a large π-conjugated rigid plane and strong electron affinity. The introduction of 2,7-alkyl plays a key role in improving the molecular weight, solubility, processability or self-assembly of such monomers or related polymers. Synthesis of 2,7-alkyl-substituted phenanthrene[9,10-b]pyrazine derivative monomers via bromination, reduction, hydroxyl protection, 2,7-alkylation, fuming nitric acid oxidative deprotection of phenanthrenequinone and ring-closing steps, the synthesis and purification are easy, and the raw material price is low, which is conducive to mass production. 2,7-Alkyl-substituted phenanthrene[9,10-b]pyrazine derivative monomers can be polymerized by Suzuki, Stille or Yamamoto to obtain homopolymers or copolymers. This series of polymers has good solubility in organic solvents, is suitable for solution processing, and has broad application prospects in the fields of organic flat panel displays, photovoltaic cells 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 Patents(China)
IPC IPC(8): C07D241/36C07D471/04C07D409/14C08G61/12C09K11/06H01L51/00H01L51/46H01L51/54H01L51/30
CPCC07D241/38C07D409/14C07D471/04C08G61/122C08G61/126C08G2261/3243C08G2261/3241C08G2261/3223C08G2261/91H10K85/111H10K85/113Y02E10/549Y02P70/50
Inventor 杨伟何锐锋张斌吴宏滨曹镛
Owner SOUTH CHINA UNIV OF TECH
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