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A kind of organic small molecule conjugated material containing isotactic bispyridine thiadiazole acceptor and its preparation method and application

A pyridinethiadiazole and small molecule technology is applied in the field of organic optoelectronic functional materials to achieve the effects of high heteroatom content, readily available raw materials and good solubility

Active Publication Date: 2021-05-11
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although pyridine thiadiazole acceptor units are widely used in the synthesis of high-performance organic / polymer semiconductor materials, D-A type organic small molecule conjugated materials containing isotactic bispyridine thiadiazole acceptors and their structural regularity control methods Still not reported, it is of great significance to develop such organic conjugated materials and explore the relationship between structural regularity and photoelectric properties

Method used

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  • A kind of organic small molecule conjugated material containing isotactic bispyridine thiadiazole acceptor and its preparation method and application
  • A kind of organic small molecule conjugated material containing isotactic bispyridine thiadiazole acceptor and its preparation method and application
  • A kind of organic small molecule conjugated material containing isotactic bispyridine thiadiazole acceptor and its preparation method and application

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Embodiment 1

[0095] A kind of organic small molecule conjugated material containing isotactic bispyridine thiadiazole acceptor of the present invention, denoted as M1, has the general structural formula of formula (I):

[0096]

[0097] Among them, Ar is R 1 For n-butyl.

[0098] The specific structural formula of M1 is:

[0099]

[0100] A synthetic route of the organic small molecule conjugated material M1 containing the isotactic bispyridine thiadiazole acceptor of this embodiment is:

[0101]

[0102] Specifically include the following steps:

[0103] (1) Synthesis of 2-butylthiophene: synthesized by the method reported in the reference (J.Am.Chem.Soc.2006,128,2336);

[0104] (2) Synthesis of 2-tributylstannyl-5-butylthiophene: synthesized by the method reported in the reference (Org. Lett. 2008, 10, 3665);

[0105] (3) Synthesis of intermediates a and b: under nitrogen protection, add 600 mg of 7-bromo-4-chloro-[1,2,5]thiadiazole-[3,4-c]pyridine into a two-neck flask (...

Embodiment 2

[0116] A kind of organic small molecule conjugated material containing isotactic bispyridine thiadiazole acceptor of the present invention, denoted as M2, has the general structural formula of formula (II):

[0117]

[0118] Among them, Ar is R 1 For n-butyl.

[0119] The specific structural formula of M2 is:

[0120]

[0121] A synthetic route of the organic small molecule conjugated material M2 containing the isotactic bispyridine thiadiazole acceptor of this embodiment is:

[0122]

[0123] The synthetic method of step (1), (2), (3) is the same as embodiment 1.

[0124] (4) Synthesis of the target product M2: under nitrogen protection, 200 mg of intermediate b (0.65 mmol), 141 mg of 1,1,1,2,2,2-hexamethylditin (0.43 mmol), bis(triphenylphosphine)palladium dichloride (0.06mmol) and 7mL of toluene solvent. After stirring at 110°C for 15 hours, the organic phase was extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, and s...

Embodiment 3

[0129] An organic small molecule conjugated material containing an isotactic bispyridine thiadiazole acceptor of the present invention, denoted as M3, has a general structural formula of formula (III):

[0130]

[0131] Among them, Ar is R 1 For n-butyl.

[0132] The specific structural formula of M3 is:

[0133]

[0134] A synthetic route of the organic small molecule conjugated material M3 containing the isotactic bispyridine thiadiazole acceptor of this embodiment is:

[0135]

[0136] The synthetic method of step (1), (2), (3) is the same as embodiment 1.

[0137] (4) Synthesis of the target product M3: under nitrogen protection, 200 mg of intermediate b (0.56 mmol), 246 mg of 1,1,1,2,2,2-hexamethylditin and ( 0.75mmol), bis(triphenylphosphine)palladium dichloride (0.03mmol) and 8mL of toluene solvent, after stirring for 1 hour at 110°C, add 174mg of intermediate a (0.56mmol) in one go, and continue at 110 After stirring at ℃ for 24 hours, the organic phase ...

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Abstract

The invention discloses an organic small molecule conjugated material containing isotactic bispyridine thiadiazole acceptor and its preparation method and application. The organic small molecule conjugated material has the following formula (I), formula (II) or formula Structural formula shown in (III). The present invention uses 7-bromo-4-chloro[1,2,5]thiadiazole[3,4-c]pyridine as raw material for the first time, and adopts reactions such as Stille coupling to synthesize the receptor containing isotactic bispyridine thiadiazole Organic small molecule conjugated materials, and provide a technical solution to control the structural regularity and photoelectric properties of bispyridine thiadiazolyl organic small molecule conjugated materials. This type of organic small molecule conjugated material has the advantages of strong electric absorption ability, large skeleton conjugation, good solubility, excellent thermal stability, and strong light absorption ability. The preparation method is simple and efficient, with good repeatability and high universality, and can be promoted. The development of more structured D‑A type organic conjugated materials has commercial prospects in the field of organic optoelectronics.

Description

technical field [0001] The invention belongs to the field of organic photoelectric functional materials, and relates to an organic small molecule conjugated material used in an organic field effect transistor device and its structural regularity control method and application, in particular to an organic compound containing an isotactic bispyridine thiadiazole acceptor. Small molecule conjugated materials and their preparation methods and applications. Background technique [0002] Compared with organic conjugated materials with random structure, structured organic conjugated materials have more ordered main chain skeleton structure, more prominent film assembly ability, wider film absorption and higher carrier mobility, etc. Advantage. In recent years, the structural regularity control of organic conjugated materials and their applications in the field of organic electronics have attracted extensive attention. Early research found that by controlling the sequence structur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00C09K11/06H01L51/54
CPCC07D519/00C09K11/06C09K2211/1092C09K2211/1029C09K2211/1066H10K85/655H10K85/6572H10K85/657
Inventor 陈华杰杜路路陶欣
Owner XIANGTAN UNIV