Spirofluorene materials containing non-benzene aromatic ring and synthesis and use thereof

An aromatic ring, non-benzene technology, applied in the field of spirofluorene oligomers and polymer materials and their preparation, can solve the problems of spirofluorene system without articles and patent reports

Inactive Publication Date: 2005-07-06
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there are no articles and patent reports on the heteroatom-containing spirofluorene system

Method used

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  • Spirofluorene materials containing non-benzene aromatic ring and synthesis and use thereof
  • Spirofluorene materials containing non-benzene aromatic ring and synthesis and use thereof
  • Spirofluorene materials containing non-benzene aromatic ring and synthesis and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1. Non-Suzuki coupling reaction Containing thiophene non-benzene aromatic ring spirofluorene unit and its oligomer trimer compound: spiro[pentacyclo[1,2-b:4,3-b']dithiophene-4 , 9'-2', 7'-(dispirobifluorene-2,2-yl)fluorene]

[0047]

[0048] 3,3-dithiophene

[0049] Add n-butyllithium (n-BuLi, 66.72mL, 106.75mmol, 1.6mol / L in Hexane, 1 equiv.) dropwise to 250mL (0.424mol / L) of -78°C tetrahydrofuran produced from acetone and dry ice; then , dropwise added 10 mL of tribromothiophene (106.75 mmol, 1 equiv.) to react for 45 minutes, then added 15.735 g (1.1 equiv.) of copper chloride at -78°C to react for one hour, then returned to room temperature and reacted for another 2 hours. The reaction was quenched with water, extracted with ether, dried and rotary evaporated, and purified by petroleum ether silica gel column to obtain 4.51 g of white crystal 3,3-dithiophene (51% yield). MS (M + =166).

[0050] 2-bromo-3,3-dithiophene

[0051] Take 2.075g (12.5mmol) ...

Embodiment 2

[0059] Example 2, Suzuki polycondensation reaction to prepare trimer oligomers containing thiophene non-benzene aromatic ring spirofluorene units: trimeric spiro[pentacyclo[1,2-b:4,3-b']dithiophene-4, 9′-fluorene]

[0060]

[0061] Take 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-spiro[pentanecyclo[1,2-b:4,3-b' ]dithiophene-4,9'-fluorene] 1.23g (1 equiv., 2.71mmol) and 2',7'-dibromospiro[pentanecyclo[1,2-b:4,3-b']dithiophene -4,9'-fluorene] 0.6597g (2.0equiv., 1.36mmol) mixed and dissolved in 20ml of toluene and tetrahydrofuran mixed solvent, add catalyst Pd (PPh 3 ) 4 (156.6mg, 5mol%), avoiding light and passing nitrogen, then adding K 2 CO 3 1.71ml 2.71ml (2mol / L, 2equiv.) reacted at 90°C for 48 hours, added water after the reaction, and used CHCl 3 Extraction, drying and rotary evaporation, petroleum ether: dichloromethane mixed solvent (5:2) silica gel column purification, to obtain white solid trimeric spiro[pentanecyclo[1,2-b:4,3-b']dithiophene-4 , 9'-fluor...

Embodiment 3

[0062] Example 3, Suzuki reaction to prepare alternating copolymers: poly(9,9-di-n-octane fluorene)-copolymerization-(9,9'-spiro[pentane[1,2-b:4,3-b'] Dithiophene-4,9'-fluorene])

[0063]

[0064] 9,9-Di-octanefluorene-2,7-bis(trimethylene borate)

[0065] Take 2,7-dibromo-9,9-n-octane fluorene (1 equiv.) and magnesium chips (2.1quiv.) in THF to react, then slowly add the Grignard reagent generated by it to the mixture made of dry ice and Acetone produced -78 ° C in excess triisopropyl borate (3.0 equiv.). After the mixture was reacted at -78°C for 2 hours, the mixture was hydrolyzed in 5% glacial sulfuric acid. Then it was extracted with ether, rotary evaporated, and finally recrystallized in n-hexane / acetone. The obtained bisboronic acid continues to react with 1,3-propanediol to generate 9,9-di-n-octane fluorene-2,7-bis(trimethylene borate) 1 H NMR (200MHz, CDCl3) δ7.78(d, J=7.7Hz, 2H), 7.72(s, 2H), 7.71(d, J=7.4Hz, 2H), 4.21(t, J=5.4Hz, 8H ), 2.12-1.94(m, 8H), 1.32...

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Abstract

The invention belongs to photoelectric material technical field, and specifically relates to a spiral fluorine oligomer containing a non-benzene aromatic ring and polymer material and preparation method thereof. The compounds are formed by introducing a non-benzene aromatic ring into highly effective luminous fluorene system through a spirane structure. The advantages of the compounds lie in that (1) the synthesis is convenient and easy, and further products modification can be carried out; (2) the compounds have high spectral stability.

Description

technical field [0001] The invention belongs to the technical field of optoelectronic materials, in particular to a spirofluorene oligomer containing a non-benzene aromatic ring, a polymer material and a preparation method thereof, and to the application of these luminescent materials in organic electroluminescence, organic field effect tubes, and organic solar energy. Applications in fields such as batteries, nonlinear optics, and lasers. 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.; Bum, 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. Organic thin film electrol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C2/00C07C13/66C07D487/04C07D495/04C09K11/06H05B33/14
Inventor 黄维解令海唐超
Owner FUDAN UNIV
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