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Material containing non-benzenoid aryl spiro and its synthesis and application

A technology of double spiro ring and benthracene, applied in the field of double spiro ring material and preparation thereof, can solve problems such as few articles and patent reports, no reports and the like

Inactive Publication Date: 2010-05-05
方圆环球光电技术盐城有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the reasons of synthesis and non-benzene structure itself, so far, few articles and patents have been reported on the heteroatom-containing spirofluorene system.
In addition, the study of heteroatom-containing double spiro rings containing non-benzene aromatic rings in the double spiro rings has not been reported, especially the thiophene structural unit

Method used

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  • Material containing non-benzenoid aryl spiro and its synthesis and application
  • Material containing non-benzenoid aryl spiro and its synthesis and application
  • Material containing non-benzenoid aryl spiro and its synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0192] Example 1. Preparation of all-thiophene double-spiro unit modules:

[0193] 3,4-Dibromo-2,5-bis(trimethylsilyl)thiophene

[0194] 3,4-dibromo-2,5-bis(trimethylsilyl)thiophene

[0195]

[0196] Lithium diisopropylamide (LDA, 2 equiv.) was added dropwise to -78°C tetrahydrofuran (0.424mol / L) produced by acetone and dry ice; then 2,5-dibromothiophene (106.75mmol, 1 equiv .) reacted for 45 minutes, then reacted at -78°C for one hour, then returned to room temperature and reacted for another 2 hours, quenched the reaction with ice water, extracted with ether, dried and rotary evaporated, and purified on a petroleum ether silica gel column to obtain white crystals 3, 4 - 4.51 g of dibromo-2,5-bis(trimethyl)thiophene (45% yield). GC-MS (EI-m / z): 386 (M + ); elemental analysis: calculated value C 10 h 18 Br 2 SSi 2 : C, 31.09; H, 4.69; S, 8.30. Measured values: C, 31.15; H, 4.74; S, 8.33.; 1 H NMR (400MHz, CDCl 3 , ppm): 0.38 (s, Me 3 Si); 13 C NMR (50.31MHz, CDCl...

Embodiment 2

[0207] Example 2, preparation of thiophene double spiro unit containing diazafluorene:

[0208]

[0209] Take 2,5-dibromo-3,4-bis(thiophen-3-yl)thiophene (2.1mmol) and magnesium Mg0.1004g (4.2mmol) to react to generate Grignard reagent, dissolve in 16mL tetrahydrofuran with 4,5- Diazofenone (4.2mmol) was reacted at 60°C for 12 hours, a large amount of white precipitate was generated, and finally saturated color NHCl was added 4 Convert Grignard salts to alcohols. After the reaction was completed, extracted with ether, dried and rotary evaporated, and purified on a silica gel column with a mixed solvent of petroleum ether:dichloromethane (3:2) to obtain a slightly yellowish white solid tertiary alcohol (yield 56%). Dissolve the above-mentioned fluorenol in glacial acetic acid, add a few drops of concentrated hydrochloric acid dropwise at 110°C for 10 minutes to form a white precipitate, add water to produce more precipitate, filter, and recrystallize with tetrahydrofuran an...

Embodiment 3

[0210] Example 3, preparation of fluorene-containing thiophene double spiro unit:

[0211]

[0212] Take 2,5-dibromo-3,4-bis(thiophen-3-yl)thiophene (2.1mmol) and magnesium Mg 0.1004g (4.2mmol) to react to generate Grignard reagent, and dissolve fluorenone (4.2mmol) in 16mL tetrahydrofuran mmol) was reacted at 60°C for 12 hours, a large amount of white precipitate was generated, and finally saturated NHCl was added 4Convert Grignard salts to alcohols. After the reaction was completed, ether was extracted, dried and rotary evaporated, and purified on a silica gel column with a mixed solvent of petroleum ether:dichloromethane (3:2) to obtain a slightly yellowish white solid tertiary alcohol (68% yield). Dissolve the above-mentioned fluorenol in glacial acetic acid, add a few drops of concentrated hydrochloric acid dropwise at 110°C for 10 minutes to form a white precipitate, add water to produce more precipitate, filter, and recrystallize with tetrahydrofuran and petroleum e...

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Abstract

The present invention belongs to the field of organic photoelectronic information material cy, and is especially one kind of high stability double spiro organic electronic material and its preparationprocess. This kind of compound contains double spiro structure module, which contains structural chain for increasing dissolubility, obstructing chromophore aggregation or increasing stability, contains non-conjugate, semi-conjugate or completely conjugate nuclear structure with four chemical bonds, and spiro center elements of C, Si or Ge. The present invention has the advantages of flexible synthesis path; effective regulation of the photoelectronic properties of the material with substituted radical, such as fluoro and dithiosulfone radical; and high configuration stability and environmentstability, such as hindered amine structure. This kind of material may find their wide application in organic plate display, photovoltaic cell, field effect tube, etc.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a double spiro ring material and a preparation method thereof, and relates to the application of these luminescent materials in the fields of organic electroluminescence, organic field effect tubes, organic solar cells, nonlinear optics, biosensors, lasers and the like. technical background [0002] Since 1987, the Tang Research Group of Kodak Company in the United States [Tang, C.W.; Van Slyke, S.A. Appl. Phys. Lett. Marks, R.N.; Mackay, K.; Friend, R.H.; Burn, P.L.; Holmes, A.B.Nature 1990, 347, 539.] published thin-film organic electroluminescent devices (Organic Light -emitting Diodes) and polymer light-emitting diodes (PolymericLight-emitting Diodes), organic flat panel display has become another generation of market-oriented display products after liquid crystal display. At the same time, other organic electronics and optoelectronic industries, i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/18C07D519/00C07D495/14C07D333/50C07D409/14C07F7/08C09K11/06H05B33/14H01L31/04H01L51/00
CPCY02E10/50
Inventor 黄维解令海
Owner 方圆环球光电技术盐城有限公司
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