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Fluorene based sulfonic acid type water/alcohol-soluble conjugated polymer and preparation method thereof

A technology of conjugated polymer and sulfonic acid type, which is applied in the field of fluorene-based sulfonic acid type water/alcohol soluble conjugated polymer and its preparation, can solve the problems of complex synthesis method and high cost, and achieve simple method and short reaction time Short, good solubility effects

Active Publication Date: 2013-11-27
江阴智产汇知识产权运营有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is: in the prior art, the synthetic method of water / alcohol-soluble conjugated polymer is complicated, and cost is high

Method used

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  • Fluorene based sulfonic acid type water/alcohol-soluble conjugated polymer and preparation method thereof
  • Fluorene based sulfonic acid type water/alcohol-soluble conjugated polymer and preparation method thereof
  • Fluorene based sulfonic acid type water/alcohol-soluble conjugated polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of sulfonic acid monomer (2,7-dibromo-9,9-bis-(3-propylamide-2-methylpropanesulfonate sodium)):

[0042]

[0043] In a 250ml four-necked flask equipped with a thermometer and a stir bar, 12.96g (40mmol) of 2,7-dibromofluorene, 0.516g (1.6mmol) of tetrabutylammonium bromide (TBAB) and 25ml of dimethylmethylene were added quantitatively. Sulfone (DMSO), slowly inject 20g of 50% sodium hydroxide solution with a syringe under a nitrogen atmosphere. After heating to 30~40℃ for 1 hour, slowly add 18.23g (0.088mol) dissolved in 40ml DMSO. ) 2-Acrylamide-2-methylpropanesulfonic acid, after dripping, react at 30-40℃ for 10h, and neutralize with hydrochloric acid. Then the solvent was evaporated to dryness by a rotary evaporator, dissolved in ethanol, filtered to remove salt, and most of the solvent was removed by a rotary evaporator, precipitated with ethyl acetate, and dried in a vacuum oven at 70°C to obtain a white powder with a yield of 78.9%.

[0044] Yield %=100%×m...

Embodiment 2

[0047] Preparation of sulfonic acid type conjugated polymer: 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborane-diyl)-9,9-dihexyl Copolymerization of fluorene and 2,7-dibromo-9,9-bis-(3-propylamide-2-methylpropanesulfonate): (PF 6 SO 3 Na)

[0048]

[0049] In a 100ml three-necked flask equipped with a thermometer and a stir bar, 0.3516g (0.6mmol) of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxa Borane-diyl)-9,9-dihexylfluorene, 0.4692g (0.6mmol) 2,7-dibromo-9,9-bis-(3-propylamide-2-) prepared in Example 1 Sodium methyl propanesulfonate), 0.004g (0.018mmol) of Pd (OAC) 2 , 0.026g (0.072mmol) P(C 6 H 12 ) 3 BF 4 , 8ml Et with a mass fraction of 25% 4 Mixed solvent of NOH and 5ml DMSO and 4.5ml toluene. They were mixed uniformly, and the reaction was stopped after reacting at 90°C for 6 hours under a nitrogen atmosphere. Then add 0.0612g (0.5mmol) of phenylboronic acid to react for 2 hours, and finally add 0.078g (0.5mmol) of bromobenzene to react for 2 hours. After the reaction was comple...

Embodiment 3

[0052] 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborane-diyl)-9,9-dioctylfluorene and 2,7-dibromo- Copolymerization of 9,9-bis-(3-propylamide-2-methylpropanesulfonate): (PF 8 SO 3 Na)

[0053]

[0054] In a 100ml three-necked flask equipped with a thermometer and a stir bar, 0.3852g (0.6mmol) of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxa Borane-diyl)-9,9-dioctylfluorene, 0.4692g (0.6mmol) 2,7-dibromo-9,9-bis-(3-propylamide-2-methylpropanesulfonic acid) Sodium), 0.004g (0.018mmol) of Pd (OAC) 2 , 0.022g (0.20mmol) DABCO, 8ml mass fraction is 25% Et 4 Mixed solvent of NOH and 6ml DMSO and 4ml toluene. They were mixed uniformly, and the reaction was stopped after reacting at 90°C for 7 hours under a nitrogen atmosphere. Then add 0.0612g (0.5mmol) of phenylboronic acid to react for 2 hours, and finally add 0.078g (0.5mmol) of bromobenzene to react for 2 hours. After the toluene and water were removed by a rotary evaporator, it was precipitated with ethyl acetate twice, and dried in a va...

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Abstract

The invention relates to the organic semiconductor field, and provides a fluorene based sulfonic acid type water / alcohol-soluble conjugated polymer and a preparation method thereof. The method comprises the following steps: reacting 2,7-dibromofluorene with an alpha, beta-unsaturated carbonyl compound under an alkaline condition to generate a sulfonic acid-containing dibromofluorene monomer; and carrying out a Suzuki reaction of the sulfonic acid-containing dibromofluorene monomer, a monomer with two ends having bromo groups and a monomer with two ends having different structures of borates under a weakly alkaline condition to synthesize the sulfonic acid-containing conjugated polymer. The sulfonate-containing functional monomer is synthesized through the above one step method, and the sulfonic acid monomer participating in the above reaction is cheap and can be easily obtained; and the polymer synthesis method has the advantages of simplicity, air insulation, no need of water insulation, and implementation of the reaction only through heating to 85-90DEG C.

Description

Technical field [0001] The invention relates to the field of organic semiconductors, in particular to a fluorene-based sulfonic acid type water / alcohol soluble conjugated polymer and a preparation method thereof. Background technique [0002] Since it was discovered in the 1970s that polyacetylene molecules were doped to make them a good conductor, more and more researchers have devoted themselves to semiconductor research. With the continuous deepening of research on organic semiconductors, it has been widely used in light-emitting diodes, solar cells, sensors, memories, resistors, capacitors, etc. With the continuous expansion of the scope of application, further requirements are put forward for the solubility of conjugated polymers. [0003] Water / alcohol soluble conjugated polymer refers to the functionalized conjugated polymer containing hydrophilic groups (anions such as sulfonate and phosphate, cations such as ammonium and non-ion such as hydroxyl) in the molecular structur...

Claims

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Application Information

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IPC IPC(8): C08G61/02C08G61/12
Inventor 李坚高山任强汪称意
Owner 江阴智产汇知识产权运营有限公司
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