Organic semiconductor material containing 6-R group- [1, 2, 5] thiazole [3, 4-g] benzotriazole and application thereof

An organic semiconductor, benzotriazole technology, applied in the field of organic photoelectric materials, can solve the problems of limited application, low yield, and many synthesis steps, and achieve the effect of easy solution processing

Active Publication Date: 2011-05-11
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, 6-R group-[1,2,5]thiazolo[3,4-g]benzotriazole, as a class of promising optoelectronic materials, has not attracted much attention, and few reports have been reported, mainly because of the fused ring There are many synthetic steps, and there are unavoidable isomers in the synthetic steps of alkyltriazoles, so that the yield is low
This greatly affects the mass preparation of its monomers, limiting its application

Method used

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  • Organic semiconductor material containing 6-R group- [1, 2, 5] thiazole [3, 4-g] benzotriazole and application thereof
  • Organic semiconductor material containing 6-R group- [1, 2, 5] thiazole [3, 4-g] benzotriazole and application thereof
  • Organic semiconductor material containing 6-R group- [1, 2, 5] thiazole [3, 4-g] benzotriazole and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0033] Example 14, Preparation of 8-dibromo-6-(2-ethyl-hexyl)-[1,2,5]thiazole[3,4-g]benzotriazole

[0034] The synthetic route is as follows:

[0035]

[0036] In the synthetic route, 4,7-dibromo-2,1,3-benzothiadiazole (a), 5,6-dinitro-4,7-dibromo-2,1,3-benzothiadiazole Synthesis of azole (b), 5,6-diamino-4,7-dibromo-2,1,3-benzothiadiazole (c) reference [Zhao.W, Cao.Y.et al.Polymer , 2010, 51, 3196-3202] and [Yi.H, Lidzey.D.et al.Maromolecular Rapid Communications.2008, 29, 1804-1809].

[0037] ① Synthesis of 4,8-dibromo-5H-[1,2,5thiazole][3,4-g]benzotriazole (d)

[0038] Add 5,6-diamino-4,7-dibromo-benzothiadiazole (2g, 6mmol) into a beaker containing 20ml of acetic acid and 20ml of aqueous solution, add tetrahydrofuran to aid in dissolution, wait until the raw materials are completely dissolved, and cool in an ice bath To 0-5 ° C, slowly add sodium nitrite aqueous solution (500 mg, 7.2 mmol), keep warm for 10 minutes, then raise the temperature to 80 ° C and stir for 1 h...

Embodiment 24

[0042] Example 24, Preparation of 8-bis(5-bromo)-dithienyl-6-(2-ethyl-hexyl)-[1,2,5]thiazole[3,4-g]benzotriazole

[0043] The synthetic route is as follows:

[0044]

[0045] In the synthetic route, 4,7-dibromo-2,1,3-benzothiadiazole (a), 5,6-dinitro-4,7-dibromo-2,1,3-benzothiadiazole The synthesis of azole (b) refers to [Zhao.W, Cao.Y.et al.Polymer, 2010, 51, 3196-3202] and [Yi.H, Lidzey.D.et al.Maromolecular Rapid Communications.2008, 29 , 1804-1809].

[0046] ① Synthesis of 5,6-amino-4,7-bis(thiophen-5-yl)-2,1,3-benzothiadiazole (II)

[0047] 5,6-dinitro-4,7-di(thiophen-5-yl)-2,1,3-benzothiadiazole (I) (3.0g, 7.7mmol) and iron powder (5.6g, 100mmol ) into 150ml of acetic acid, stirred at 80°C for 4 hours, then poured into 500ml of water. The crude product was washed twice with distilled water to obtain yellow powder (II) with a yield of 87%.

[0048] 1 H-NMR (CDCl3, 300 mHz, ppm): δ 7.56 (dd, 2H), 7.36 (dd, 2H), 7.25 (t, 2H), 4.39 (4H).

[0049] 13 C-NMR (CDCl3, ...

Embodiment 3

[0060] Example 3 Poly{N-9-heptadecyl-2,7-carbazole-alternating-4,8-bis(5-bromo)-dithienyl-6-(2-ethyl-hexyl)- Synthesis of [1,2,5]thiazole[3,4-g]benzotriazole} (abbreviated as P3ZBTTT-C17CZ)

[0061] The synthetic route is as follows:

[0062]

[0063] Monomer 4,8-bis(2-bromo-dithiophen-5-yl)-(2-ethyl-hexyl)-[1,2,5]thiazolo[3,4-g]benzotriazole ( V) (0.152g, 0.25mmol) with the monomer 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-N-9- Heptadecylcarbazole (VI) (0.1635g, 0.25mmol) and palladium tetraphenylphosphine (6mg) were added into a 25ml two-necked bottle, and then 10ml of toluene was added to fully dissolve them. Another 1ml of base 336 and 1ml of deionized water were injected into it. After nitrogen protection for 20 minutes, the temperature was raised to 85° C., and the reaction was carried out for 12 hours. Then, it was cooled to room temperature under the protection of nitrogen, and the reactant was dropped into 500 ml of methanol to precipitate out, and ...

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Abstract

The invention provides an organic semiconductor material containing 6-R group-[1, 2, 5] thiazole [3, 4-g] benzotriazole and an application thereof. Diazosulfide is used as parent, benzotriazole derivatives are formed by reduction and ring closure of nitrated diazosulfide, and finally, a halogenated 6-R group-[1, 2, 5] thiazole [3, 4-g] benzotriazole monomer is synthesized by performing alkylation reaction on an H of an N atom; and the monomer is reacted with a monomer containing an aromatic group under effect of metal catalyst to prepare the organic semiconductor material. Positions 1, 2, 5 and 6 of a benzene ring of the organic semiconductor material are respectively connected with alkyl triazole and thiazole, the two kinds of chemical groups have excellent electron attracting performance, and a formed ternary condensed ring has better planarity and conjugated bonds, and also has good dissolubility. The organic semiconductor material provided by the invention can be used as an active layer having application foreground to be applied in organic photoelectric devices.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to the design and preparation of an organic semiconductor material containing 6-R group-[1,2,5]thiazole[3,4-g]benzotriazole, and to The application of this kind of materials in organic field effect transistors, organic solar cells, organic electroluminescence and other organic optoelectronic technologies. 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/30H01L51/46H01L51/54
CPCY02E10/549
Inventor 黄飞董杨曹镛
Owner SOUTH CHINA UNIV OF TECH
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