Bifurcate alkyl chain and preparation and application thereof in organic conjugated molecules

A technology of alkyl and alkoxy, which is applied in the preparation of new bifurcated alkyl chains, organic electronic materials and their preparation, and can solve the problem of low polymer mobility

Active Publication Date: 2012-11-14
PEKING UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In view of the current research results of polymer field effect transistor materials and the problem of relatively low mobility of polymers in the research of solar cell materials, the purpose of the present invention is to provide a new type of forked alkyl chain and apply it to organic conjugated Molecules, especially in the preparation of organic conjugated polymers

Method used

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  • Bifurcate alkyl chain and preparation and application thereof in organic conjugated molecules
  • Bifurcate alkyl chain and preparation and application thereof in organic conjugated molecules
  • Bifurcate alkyl chain and preparation and application thereof in organic conjugated molecules

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Experimental program
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Effect test

Embodiment 1

[0146]

[0147] The synthetic process of compound 1: add (60g, 0.79mol) 1,3-propanediol in 500ml round-bottomed flask, then add (17.7g, 0.32mol) KOH solid therein, to remove trace moisture in 1,3-propanediol . With stirring at 90°C, add (39.8 g, 0.32 mol) benzyl chloride to 1,3-propanediol using a dropping funnel. Afterwards, the temperature was raised to 130°C for 2 hours, and the reaction was stopped and cooled to room temperature. After the organic phase was extracted by water / ether separation, the solvent was removed by rotary evaporation under reduced pressure, and 39.8 g of a colorless oily product was obtained by distillation under reduced pressure with a yield of 77%. Compound 1. 1 H NMR (CDCl 3 , 400MHz, ppm) δ: 7.36-7.28(m, 5H), 4.51(s, 2H), 3.79-3.75(m, 2H), 3.66-3.64(t, J=5.5Hz, 2H), 2.44(br, s, 1H), 1.88-1.83 (m, 2H).

Embodiment 2

[0149]

[0150] The synthesis process of compound 2: at 0°C, (40g, 0.44mol) 1,4-butanediol was added to 200ml of dry THF, and (5.3g, 0.22mol) sodium hydride was added in batches within 30min, Return to room temperature and react for 2h. Dissolve (38g, 0.22mol) benzyl bromide in 20ml THF, drop it into the above system at 0°C, and then reflux the system for 4h. After the reaction, quench the reaction with cold water, and extract the organic phase with ether. The organic phase was dried with anhydrous sodium sulfate and filtered, and then the solvent was removed by rotary evaporation under reduced pressure, and then 28.1 g of colorless oily liquid 2 was obtained by distillation under reduced pressure with a yield of 71%. 1 H NMR (CDCl 3 , 400MHz, ppm) δ: 7.36-7.26(m, 5H), 4.52(s, 2H), 3.65-3.61(m, 2H), 3.53-3.50(t, J=5.3Hz, 2H), 2.36(br, s, 1H), 1.73-1.65 (m, 4H).

Embodiment 3

[0152]

[0153] The synthesis process of compound 3: at 0°C, (40g, 0.39mol) 1,5-pentanediol was added to 200ml dry THF, and (4.6g, 0.19mol) sodium hydride was added in batches within 30min, Return to room temperature and react for 2h. Dissolve (33g, 0.19mol) benzyl bromide in 20ml THF, drop it into the above system at 0°C, and then reflux the system for 4h. After the reaction, quench the reaction with cold water, and extract the organic phase with ether. The organic phase was dried with anhydrous sodium sulfate and filtered, then the solvent was removed by rotary evaporation, and then 23.1 g of colorless oily liquid 3 was obtained by distillation under reduced pressure with a yield of 62%. 1 HNMR (CDCl 3 , 400MHz, ppm) δ: 7.36-7.26(m, 5H), 4.50(s, 2H), 3.64-3.61(t, J=6.5Hz, 2H), 3.50-3.64(t, J=6.5Hz, 2H) , 1.68-1.54(m, 4H), 1.49-1.43(m, 2H).

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Abstract

The invention discloses a bifurcate alkyl chain and a preparation and an application thereof in organic conjugated molecules. The bifurcate alkyl chain serving as a solubilization group is applied in preparing organic conjugated molecules (particularly organic conjugated polymers), the interval number m of a formed alkyl side chain and main methylene is larger than one, capable of reducing effects of the alkyl chain on main Pi accumulation, so that the solubility of the organic conjugated molecules is guaranteed, and the mobility ratio of current carriers is improved greatly, the bifurcate alkyl chain is suitable for being used as organic semiconductor materials in photoelectric devices of organic field effect transistors, organic solar cells, organic light emitting diodes and the like.

Description

technical field [0001] The invention relates to a preparation method of a novel branched alkyl chain, in particular to a class of organic electronic materials with branched alkyl chains and a preparation method thereof, belonging to the fields of organic functional materials and organic electronics. Background technique [0002] The structure of organic conjugated molecules contains a conjugated system composed of delocalized π electrons, so it reflects special properties such as light, electricity, and magnetism, which has attracted widespread attention from scientists and has become an important topic in the past 20 years. research hotspot in recent years. The synthesis and functional device-based research of organic conjugated molecules involves many disciplines such as chemistry, physics, electronics, and materials science. It is a frontier field of interdisciplinary research, full of vitality and opportunities, and is also one of the important directions for the future ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C31/02C07C29/00C07C19/07C07C17/16C07C211/03C07C209/42C07C247/04C07D209/34C08G61/12H01L51/30H01L51/46H01L51/54
CPCC07D207/34C07D209/34H01L51/0036Y02E10/549C07D417/14H10K85/113C07C31/02H10K10/46H10K30/00H10K50/11C07C17/16C07C19/07C07C29/151C07C209/42C07C211/03C07C247/04
Inventor 裴坚雷霆窦锦虎
Owner PEKING UNIV
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