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Thiophene compound having sulfonyl group and process for producing the same

A technology of sulfonyl thiophene and bis-sulfonyl thiophene, which is applied in the field of thiophene compounds and its preparation, can solve the problems of difficult control of coating film thickness and low solid concentration

Inactive Publication Date: 2008-10-08
NISSAN CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] However, polythione-based conductive polymers come with the problem that they can be stably dispersed at extremely low solid concentrations, thus making it difficult to control the thickness of each coating film

Method used

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  • Thiophene compound having sulfonyl group and process for producing the same
  • Thiophene compound having sulfonyl group and process for producing the same
  • Thiophene compound having sulfonyl group and process for producing the same

Examples

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preparation example Construction

[0449] The preparation method comprising the above-mentioned steps 1 to 5-1 or 5-2 is most suitable for synthesizing wherein R 50 and R 51 Is the method of the compound of hydrogen atom.

[0450] No particular limitation is imposed on the production methods of the sulfonylthiophene oligomer compounds respectively represented by the general formulas [2] and [16], and the sulfonylbithiophene compounds respectively represented by the general formulas [19]-[22], they It can be obtained by converting the terminal substituent of the sulfonylthiophene compound represented by the general formula [1] or [24] into an appropriate substituent, and then causing coupling by a desired method described later herein. As for the obtained compounds represented by the general formulas [2] and [16] respectively, the terminal substituents of their thiophene rings (or other spacers represented by the general formulas [3]-[11] respectively) can be converted into suitable The substituents can then b...

Embodiment 13

[0541] [Example 1] 3, the synthesis of 4-bissulfonylthiophene

[0542] [chemical formula 88]

[0543]

[0544] 3,4-disulfanylthiophene compound 1a-f and ruthenium(III) chloride n-hydrate (0.05 equiv, commercial product) were added to the reaction vessel and stirred at room temperature until they were completely dissolved. The reaction vessel was cooled and sodium periodate (4.20 equiv, commercial product) was added in portions while keeping the solution at room temperature and watching for exotherm. After the addition was complete, the mixture was further stirred at room temperature for 5 hours. The reaction mixture was extracted with diethyl ether. The organic layer was washed three times with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained crude product was purified by silica gel column (ethyl acetate:hexane=1:2) to obtain the corresponding compound as a white solid 2a-f .

[0545] Table 1

[0546]

[0547] *AcO...

Embodiment 2

[0572] [Example 2] 3,4-bissulfonyl-2, the synthesis of 5-bis(tributylstannyl)thiophene

[0573] [chemical formula 89]

[0574]

[0575] The 3,4-bissulfonylthiophene obtained above 2a-f One was placed in a reaction vessel and then dissolved in THF under a nitrogen atmosphere. The solution was cooled to -78°C. n-Butyllithium (1.58M hexane solution, 2.20 equivalents, commercial product) was gradually added dropwise, and the resulting mixture was stirred at the same temperature for 1 hour. Subsequently, tributylstannyl chloride (2.50 equivalents, commercial product) was added dropwise, followed by stirring for 3 hours. After completion of the reaction, disodium hydrogen phosphate / sodium dihydrogen phosphate buffer adjusted to pH 7 was added to terminate the reaction, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed, and the resulting crude product w...

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Abstract

A thiophene compound having sulfonyl groups which is represented by the formula [1]. It has high heat resistance and high unsusceptibility to oxidation and can improve solubility and dispersibility in various solvents. [In the formula, R1 and R2 each independently represents hydrogen, halogeno, cyano, etc.; and R3 and R3' each independently represents C1-20 alkyl, C1-20 haloalkyl, phenyl optionally substituted by W, thienyl optionally substituted by W, etc. (W represents chlorine, etc.)].

Description

technical field [0001] The present invention relates to a sulfonyl-containing thiophene compound and a preparation method thereof, more specifically, to sulfonyl-containing thiophene monomers, oligomers and polymers and their preparation methods. Background technique [0002] In recent years, aromatic compounds and heterocyclic compounds having π-conjugated systems have been used in various electronic devices such as organic electroluminescent devices, batteries and semiconductors due to their light-emitting characteristics and electron / hole transport ability characteristics. [0003] Organic electroluminescence devices can be broadly classified into high-molecular devices and low-molecular devices. Since a sufficient degree of available carrier mobility and suitable fluorescence emission characteristics are required, especially for low-molecular devices, it is required to freely vary the bandgaps of their derivatives in the development of π-conjugated compounds. Their thin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/34C08G61/12C09K11/06H01L51/05H01L51/30H01L51/50
CPCH01L51/5012C08G61/126H01L51/0036Y02E10/549C07D333/34Y02P70/50H10K85/113H10K50/11H10K50/805
Inventor 垣内畅之古性均大谷直树冈内辰夫中家直树
Owner NISSAN CHEM CORP
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