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9-hydroxyl-9'-aromatic conjugate substituted fluorene-containing polymer material and preparation and application methods thereof

A polymer material, polymer technology, applied in chemical instruments and methods, luminescent materials, semiconductor/solid-state device manufacturing, etc., to achieve mild conditions and simple synthesis steps

Inactive Publication Date: 2011-08-31
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the patent of the fluorene structural unit conjugated polymer containing a hydroxyl substituent at the 9-position.

Method used

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  • 9-hydroxyl-9'-aromatic conjugate substituted fluorene-containing polymer material and preparation and application methods thereof
  • 9-hydroxyl-9'-aromatic conjugate substituted fluorene-containing polymer material and preparation and application methods thereof
  • 9-hydroxyl-9'-aromatic conjugate substituted fluorene-containing polymer material and preparation and application methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1, poly(9-octyloxybenzene-9'-hydroxyl-fluorene)

[0042] Poly(9-(4-(octyloxy)phenyl)-9H-fluoren-9-ol)

[0043] p-bromooctyloxybenzene

[0044] 1-romo-4-(octyloxy)benzene

[0045] Experimental procedure: Dissolve p-bromophenol (1 equiv) in acetone, add potassium carbonate and a small amount of tetrabutylammonium bromide, heat to reflux at 70°C, add bromooctane (1.5 equiv) dropwise, react for 24 hours, adjust The pH value was neutral, the liquid was separated with dichloromethane, and passed through the column by rotary evaporation to obtain a transparent liquid (yield 80.5%).

[0046] GC-MS (EI-m / z): 284 (M + ).

[0047] 2,7-Dibromo-9-p-octyloxybenzene-9′-hydroxyl-fluorene

[0048] 2,7-dibromo-9-(4-(octyloxy)phenyl)-9H-fluoren-9-ol

[0049] Experimental procedure: under the protection of nitrogen, take p-bromooctyloxybenzene (1.2equiv) and magnesium (1.5equiv) (reaction to generate Grignard reagent), and 2,7-dibromo-9-fluorene dissolved in 100ml of tetrahy...

Embodiment 2

[0055] Embodiment 2, poly(9-(3-hexylthiophene)-9'-hydroxyfluorene)

[0056] Poly(9-(4-(octyloxy)phenyl)-9H-fluoren-9-ol)

[0057] 2,7-Dibromo-9-(3-bromothiophene)-9′-hydroxyfluorene

[0058] 2,7-dibromo-9-(3-bromothiophen-2-yl)-9H-fluoren-9-ol

[0059] Experimental procedure: under the protection of nitrogen, add a mixture of tetrahydrofuran (THF), 2,3-dibromothiophene (1.2 equiv) and magnesium ((1.5 equiv)) into the dropping funnel, drop 2d 2 into the flask, 3-dibromothiophene, rapid initiation, ice bath quickly after initiation, then add THF to the flask, slowly add 2,3-dibromothiophene dropwise, after dropwise addition, reflux at 40°C for 2h to prepare lattice reagent. Add 2,7-dibromo-9-fluorenone (1.0 equiv) and THF into another constant pressure dropping funnel, add the prepared Grignard reagent dropwise under ice bath, after the dropwise addition, reflux at 40°C for 24h . with saturated NH 4 Cl quenched the reaction slowly under ice bath, added dichloromethane (DCM)...

Embodiment 3

[0068] Example 3, poly-{[2,7-(9-octyloxybenzene-9'-hydroxyl-fluorene)]-1,6-[pyrene]}

[0069] Poly-{[2,7-(9-(4-(octyloxy)phenyl)-9H-fluoren-9-ol])]-1,6-[pyrene]}

[0070] Experimental procedure: Mix and dissolve 2,7-dibromo-9-p-octyloxybenzene-9'-hydroxy-fluorene (1equiv) and pyrene-1,6-diboronic acid butyl ester (1equiv) in 20ml of toluene and tetrahydrofuran In the mixed solvent, add the catalyst Pd(PPh 3 ) 4 (1-5% of monomer molar weight). Protect from light and pass through nitrogen, then add K 2 CO 3 (2equiv.), react at 90°C for 48 hours, add water after the reaction, use CHCl 3 Extract, dry and concentrate by rotary evaporation, and put into 100mL of methanol. The mixture was suction-filtered, purified by alumina chromatography, concentrated, put into 500ml of methanol, precipitated by suction-filtration, and the collected solid was purified in a Soxhlet purifier for 3 days, re-precipitated in methanol, and dried to obtain a powder product . GPC: M n = 17250; PD...

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Abstract

A 9-hydroxyl-9'-aromatic conjugate substituted fluorene-containing polymer material and preparation and application methods thereof belong to the fields of photoelectric materials and organic information display science and technology, and in particular relates to a 9-hydroxyl-9'-aromatic conjugate substituted fluorene-containing homopolymerized or copolymerized conjugate polymer, a preparation method thereof and application of the material to the field of organic electronics such as organic light emitting display and the like. The material has the following structure which is shown in the specification. The material has the advantages that: (1) the synthesis steps are simple and the conditions are mild; (2) the advantages of high thermal stability, glass transition temperature and the like are kept; and (3) the material shows morphological diversity due to a supramolecular effect and has rich optical characteristic. It can be anticipated that the material will become an organic photoelectric function material with commercial potential.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. It specifically relates to a 9-hydroxyl-9'-containing aromatic conjugated substituted fluorene material and its preparation method, and relates to the application of these materials in organic electroluminescence, organic optical storage, organic field effect tubes, organic solar cells, and organic nonlinear optics , chemical and biological sensing and organic laser applications. Background technique [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 Polymeric Light-emitting Diodes (Polymeric Light-emitting Diodes), organic flat panel display has become another generation of market-oriented display products after liqu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02C08G61/12C09K11/06H01L51/30H01L51/46H01L51/54
CPCY02E10/50Y02E10/549
Inventor 解令海黄维林进义张超林宗琼仪明东
Owner NANJING UNIV OF POSTS & TELECOMM
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