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Triphenylamine benzothiadiazole polymer containing biphenyl structure as well as preparation method and application thereof

A technology of benzothiadiazole and biphenyl structure, which is applied in the field of triphenylamine benzothiadiazole polymers, can solve the problems of poor heat resistance and low solubility, and achieve increased solubility, good solubility, and discoloration obvious effect

Active Publication Date: 2020-04-17
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to solve the problems of low solubility and poor heat resistance of organic small molecule compounds in organic solvents in the existing optoelectronic field, and propose a triphenylamine-based benzothiadiazole polymer containing a biphenyl structure and its preparation Method and application in electrochromic

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  • Triphenylamine benzothiadiazole polymer containing biphenyl structure as well as preparation method and application thereof
  • Triphenylamine benzothiadiazole polymer containing biphenyl structure as well as preparation method and application thereof
  • Triphenylamine benzothiadiazole polymer containing biphenyl structure as well as preparation method and application thereof

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specific Embodiment approach 1

[0047] Specific embodiment 1: The triphenylamine-based benzothiadiazole polymer containing biphenyl structure in this embodiment is carbazolyl triphenylamino-benzothiadiazole polymer containing biphenyl structure, bis-4 containing biphenyl structure - tert-butyltriphenylaminobenzothiadiazole polymer or triphenylaminobenzothiadiazole polymer containing biphenyl structure;

[0048] Wherein the structural formula of the carbazolyl triphenylamino-benzothiadiazole polymer containing biphenyl structure is:

[0049] In the formula, n is a positive integer;

[0050] The structural formula of two 4-tert-butyltrianilinobenzothiadiazole polymers containing biphenyl structure is:

[0051] In the formula, n is a positive integer.

[0052] The structural formula of the triphenylamino-benzothiadiazole polymer containing biphenyl structure is:

[0053] In the formula, n is a positive integer.

[0054] This embodiment has the following beneficial effects:

[0055] 1. The triphenylam...

specific Embodiment approach 2

[0060] Specific embodiment two: the method for the triphenylamine benzothiadiazole polymer containing biphenyl structure in this embodiment is carried out according to the following steps:

[0061] 1. Preparation of benzothiadiazole derivatives:

[0062] Add the compound 4,7-dibromo-2,1,3-benzothiadiazole and n-butyllithium with a concentration of 1.6-1.7M to the degassed tetrahydrofuran at -79~-78°C, and heat up to Stir at -40°C for 3 to 4 hours under a nitrogen atmosphere, then cool down to -79 to -78°C, add tributyltin chloride, heat up to room temperature and stir for 17 to 18 hours, quench the reaction with water, use The organic phase was obtained by ether extraction, and anhydrous MgSO was added to the organic phase 4 After drying, the organic phase is evaporated under reduced pressure to obtain the benzothiadiazole derivative M1;

[0063] The molar volume ratio of compound 4,7-dibromo-2,1,3-benzothiadiazole to degassed tetrahydrofuran in step 1 is 0.2mmol:(19~20)mL:;...

specific Embodiment approach 3

[0073] Specific embodiment three: the difference between this embodiment and specific embodiment two is: the preparation method of the degassed tetrahydrofuran described in step one is: vacuumize the three-neck round bottom flask filled with tetrahydrofuran with a vacuum pump, and then pass it into Nitrogen: Repeat vacuuming and feeding nitrogen 3 to 4 times. Others are the same as in the second embodiment.

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Abstract

The invention discloses a triphenylamine benzothiadiazole polymer containing a biphenyl structure as well as a preparation method and an application thereof. The triphenylamine benzothiadiazole polymer aims to solve the problems of low solubility and poor heat resistance of small organic molecule compounds in organic solvents in the existing photoelectric field. The preparation method comprises the following steps: firstly, taking 4-(9H-carbazole-9-yl) aniline, N', N'-bis(4-(tert-butyl) phenyl) benzene-1, 4-diamine and 4-amino triphenylamine monomers as raw materials, and carrying out a substitution reaction on the raw materials and p-bromoiodobenzidine to generate triphenylamine monomers containing biphenyl structures; the benzothiadiazole derivative is prepared by the following steps: substituting two bromides on 4, 7-dibromo-2, 1, 3-benzothiadiazole with tributyltin chloride to form a reaction active site, and reacting the reaction active site with a triphenylamine monomer containing a biphenyl structure to generate the polymer. The triphenylamine benzothiadiazole polymer is easily soluble in polar solvents and good in thermal stability, and is applied to the field of multifunctional materials.

Description

technical field [0001] The invention relates to a triphenylamine benzothiadiazole polymer containing a biphenyl structure, a preparation method and application thereof. Background technique [0002] Conjugated polymers containing triphenylamine structures have received extensive attention in the past few decades due to their diverse optoelectronic and redox properties. Their π-conjugated backbones provide a wide range of delocalized electronic structures, which endow them with unique optoelectronic properties compared to conventional polymers. In addition, conjugated polymers can be processed by solution casting or printing techniques, and their color and bandgap can be finely tuned through structural control. Small molecule organic semiconductors are usually processed by high vacuum vapor deposition. Therefore, compared with small-molecule organic devices, organic electronic devices based on conjugated polymers have the advantages of simple fabrication and low production ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K9/02G01J1/42G01N21/64G01N21/78
CPCC08G61/123C09K9/02G01N21/643G01N21/78G01J1/42C09K2211/1483C09K2211/1433C08G2261/54C08G2261/124C08G2261/18C08G2261/3246C08G2261/3162C08G2261/414Y02E10/549
Inventor 牛海军林晓雪高艳雨
Owner HEILONGJIANG UNIV
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