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Organic semiconductor material containing naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole and application thereof

An organic semiconductor, 2-c technology, applied in the application field of organic photoelectric technology, can solve the problems of difficult purification, limited application, low electron cloud density of aromatic ring, etc., and achieve cost reduction, solubility and planar balance, good Effect of solution processability

Active Publication Date: 2011-05-18
SOUTH CHINA UNIV OF TECH
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Problems solved by technology

[0005] However, naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole has not attracted attention, and there are few reports, the main reason is that naphthalene[1,2-c:5,6 -c] bis[1,2,5]thiadiazole has strong electron deficiency, low electron cloud density of aromatic ring, poor chemical reactivity, and difficult substitution reaction, so it is difficult to modify its structure, which greatly affects its In addition, naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole has a large plane in its structure, and the molecules are easy to aggregate, resulting in poor solubility of its derivatives, especially It is that its halides can neither be prepared in large quantities nor purified, which limits its application

Method used

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  • Organic semiconductor material containing naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole and application thereof
  • Organic semiconductor material containing naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole and application thereof
  • Organic semiconductor material containing naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole and application thereof

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preparation example Construction

[0036] The preparation of the organic semiconductor material of the present invention: directly halogenate naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole, and introduce alkylated thiophene or bithiophene and other auxiliary The aromatic group Ar of the soluble group reacts with the halogenated product through a transition metal-catalyzed coupling reaction to obtain a naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole structure Organic semiconductor materials. Using the aromatic group Ar as a bridge, the solubility of Ar can be adjusted, and active groups can also be introduced at the reactive sites on the Ar group. In this way, the problems of solubility and chemical modification of naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole are solved, better performance is obtained, and the problem of naphthalene [1,2-c:5,6-c]bis[1,2,5]thiadiazole processability problem, expanding naphthalene[1,2-c:5,6-c]bis[1,2 , The reactivity and application of this structure of 5] thiadiazole can obtain a...

Embodiment 13

[0039] Example 13, Preparation of 7-dithiophene-naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole

[0040] The synthetic route is as follows:

[0041]

[0042] (1) Preparation of 3,7-dibromo-naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole

[0043] Add 0.49g (2mmol) of naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole into a 50ml single-necked bottle with a stirring bar, and add 10ml of concentrated sulfuric acid, stir to dissolve and Heat to 60°C, then add 0.78g NBS (4.4mmol), and react in the dark for 24 hours. After the reaction, pour the reaction solution into water, and the precipitated solid is the crude product. Filter, wash with water until neutral, and then wash with ethanol After washing and drying, 0.72 g of crude product was obtained, which was directly carried out to the next reaction without purification.

[0044] (2) Preparation of 3,7-bis(thiophen-5-yl)-naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole

[0045] Add 0.72g of 3,7-dibromo-naphthalene[1,2-c:5,6-c]bis[1,2,5]...

Embodiment 2

[0046] Example 2 Poly{N-9-heptadecyl-2,7-carbazole-alternating-2,2-[3',7'-bis(3-octylthiophen-5-yl)-naphthalene[1 ', 2'-c: 5', 6'-c] two [1', 2', 5'] thiadiazole]} (abbreviated as PCz-DOTNBT) preparation

[0047] The synthetic route is as follows:

[0048]

[0049] 3-octyl-5-tributyltinthiophene reagent was prepared according to literature [Voituriez, Arnaud; Mellah, Mohamed; Schulz, Emmanuelle.Synthetic Metals 2006, 156 (2-4), 166-175.], 2,7-bis( 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-diyl)-N-9-heptadecylcarbazole According to literature [N.Blouin, A.Michaud, M . Leclerc, Adv. Mater. 2007, 19, 2295-2300] Preparation.

[0050] (1) Preparation of 3,7-dibromo-naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole

[0051] Add 0.73g (3mmol) of naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole into a 50ml single-necked bottle with a stirring bar, and add 10ml of concentrated sulfuric acid, stir to dissolve And heated to 60 ℃, then add 1.17g (6.6mmol) NBS, avoid light reaction, thin chr...

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Abstract

The invention relates to an organic semiconductor material containing naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole and application thereof, wherein the organic semiconductor material is prepared by reacting the halogenated derivatives with the monomer containing an aromatic group structure under the metal catalyst, wherein the halogenated derivatives are obtained by halogenating the naphthalene [1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole; the aromatic group is connected with a naphthalene [1, 2-c:5, 6-c] di [1, 2, 5] thiadiazole unit in a conjugate manner. The organic semiconductor material is characterized by containing 3, 7 substituted decorative[1, 2-c: 5, 6-c] di [1, 2, 5] thiadiazole chemical groups; as the naphthalene [1, 2-c:5, 6-c] di [1, 2, 5] thiadiazole has excellent electron-withdrawing ability and planarity, the organic semiconductor material can excellently adjust the photoelectric property, has excellent photoelectric performance, and is applied to the field of organic photoelectric components.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to a class of organic semiconductor materials containing naphthalene[1,2-c:5,6-c]bis[1,2,5]thiadiazole and its application in the field of organic photoelectric technology Applications. Background technique [0002] Organic photoelectric materials and devices are very suitable for industrial production and promotion due to their easy-to-obtain materials, simple preparation process, low cost, flexibility, and large-area film formation, and have very broad commercialization prospects. Since 1987, Deng Qingyun Research Group [Tang, C.W.; Van Slyke S.A.et.al; Appl.Phys.Lett.1987, 51, 913.] of Kodak Company of the United States proposed an organic small molecule thin film electroluminescent device and in 1990, Cambridge, UK Since the R.H.Friend research group [Burroughes, J.H.; Bradley, D.D.C.; Friend, R.H; Holmes, A.B.et al; Nature 1990, 347, 539.] proposed the ...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/54H01L51/30H01L51/46
CPCY02E10/50Y02E10/549
Inventor 黄飞曹镛王明
Owner SOUTH CHINA UNIV OF TECH
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