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Double spiro material containing heteroaton and its synthetic method and use

A heteroatom, double spiro ring technology, applied in the field of heteroatom-containing double spiro ring materials and their preparation, can solve the problems of no articles and patent reports, etc.

Inactive Publication Date: 2006-03-22
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, patents containing double-spiro ring materials based on the all-benzene structure have been reported, but there are no articles and patent reports on the thiophene double-spiro ring material system containing heteroatoms

Method used

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  • Double spiro material containing heteroaton and its synthetic method and use
  • Double spiro material containing heteroaton and its synthetic method and use
  • Double spiro material containing heteroaton and its synthetic method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Embodiment 1, thiophene double spiro compound material:

[0084] Disspiro[9H-fluorene-9,1′(3′H)-bisindene[2,1-b:1′,2′-d]thiophene-3′,9″-[9H]fluorene]

[0085] Dispiro[9H-fluorene-9,1′(3′H)-diindeno[2,1-b:1′,2′-d]thiophene-3′,9″-[9H]fluorene]

[0086] 3,4-Diphenylthiophene

[0087] 3,4-diphenylthiophene

[0088] Under nitrogen atmosphere, take magnesium Mg chips (1equiv.) and a little I 2 Mix, slowly drop bromobenzene into the reaction flask at 35°C, and reflux the reaction for 20 minutes; cool the reaction and slowly transfer the formed Grignard reagent to the reaction flask containing the catalyst Ni(dppp)Cl using a transfer tube. 2 and 3,4-dibromothiophene in a reaction flask, added to reflux for 24 hours, diluted with ice water, extracted with ether, dried and rotary evaporated, and purified by petroleum ether silica gel column to obtain colorless crystals (yield 78.8%).

[0089] mp 115-116°C (lit.112-113°C);

[0090] Elemental Analysis: C 16 h 12 S, measured ...

Embodiment 2

[0108] Embodiment 2, tetrabromothiophene double spiro compound module:

[0109] 2,2",7,7"-Tetrabromo-dispiro[9H-fluorene-9,5'(7'H)-diindene[2,1-b:1',2'-d]thiophene- 7',9"-[9H]fluorene]

[0110] 2,2",7,7"-tetrabromo-dispiro[fluorene-9,5'(7'H)-diindeno[2,1-b:1',2'-d]thiophene-7',9"- fluorene]

[0111] Take 2,5-dibromo-3,4-diphenylthiophene (2.1mmol) and magnesium Mg0.1004g (4.2mmol) to react to generate Grignard reagent, and dissolve 2,7-dibromofluorenone ( 4.2mmol) was reacted at 60°C for 24 hours, a large amount of white precipitate was generated, and finally saturated color NHCl was added 4 Convert Grignard salts to alcohols. After completion of the reaction, extracted with ether, dried and rotary evaporated, and purified on a silica gel column with a mixed solvent of petroleum ether:dichloromethane (4:1) to obtain a slightly yellowish white solid tertiary alcohol (yield 34%). Dissolve the above-mentioned fluorenol in glacial acetic acid, add a few drops of concentrated ...

Embodiment 3

[0113] Embodiment 3, dibromothiophene double spiro compound module:

[0114] 2,2″-Dibromo-dispiro[9H-fluorene-9,5′(7′H)-bisindene[2,1-b:1′,2′-d]thiophene-7′,9″ -[9H]fluorene]

[0115] 2,2″-dibromo-dispiro[fluorene-9,5′(7′H)-diindeno[2,1-b:1′,2′-d]thiophene-7′,9″-fluorene]

[0116] Take 2,5-dibromo-3,4-diphenylthiophene (2.1mmol) and magnesium Mg0.1004g (4.2mmol) to react to generate Grignard reagent, and dissolve 2-bromofluorenone (4.2mmol) in 16mL tetrahydrofuran React at 60°C for 24 hours, a large amount of white precipitates are formed, and finally add saturated NHCl 4 Convert Grignard salts to alcohols. After the reaction was completed, ether was extracted, dried and rotary evaporated, and dichloromethane solvent was purified on a silica gel column to obtain a slightly pale yellow white solid tertiary alcohol (yield 35.6%). Dissolve the above-mentioned fluorenol in glacial acetic acid, add a few drops of concentrated hydrochloric acid dropwise at 110°C for 10 minutes t...

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Abstract

The present invention belongs to the field of photoelectronic material technology, and is especially double spiro material containing hetero atom and its preparation process and application in organic plate display, photovoltaic cell, organic FET, laser and other organic electronics fields. The compounds are conjugate semiconductor material with double spiro structure introduced hetero atom. The double spiro material has the advantages of simple synthesis, capacity of further modification, effective realization of the photoelectronic property of modulation material, high heat stability, high vitrification point, etc. The material of the present invention may be used in producing photoluminescent device with satisfied brightness and light emitting efficiency, and has commercial application latent.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a heteroatom-containing double spiro ring material and a preparation method thereof, and relates to the application of this type of material in the fields of organic electroluminescence, organic field effect tube, organic solar cell, nonlinear optics, biosensing, laser 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 (Polymeric Light-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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/78C07D521/00C07D333/50C07D209/96C07D307/77C07D495/22C07D491/22C07D471/22C07F7/08H01L31/04H01L51/30H01L51/42H01L51/50H05B33/14C09K11/06
Inventor 黄维解令海侯晓雅
Owner FUDAN UNIV
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