Organic semiconductor material containing dibenzothiophene sulfone, and preparation method and application thereof

A technology of organic semiconductor and thiophene sulfone, which is applied in the field of organic semiconductor materials, can solve problems such as device instability and achieve the effect of improving luminous efficiency

Active Publication Date: 2012-12-26
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Anthracene single crystal is the earliest used blue organic electro...

Method used

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  • Organic semiconductor material containing dibenzothiophene sulfone, and preparation method and application thereof
  • Organic semiconductor material containing dibenzothiophene sulfone, and preparation method and application thereof
  • Organic semiconductor material containing dibenzothiophene sulfone, and preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0042] The preparation method of the above-mentioned dibenzothiophene sulfone-containing organic semiconductor material, such as figure 1 As shown, the process steps are as follows:

[0043] Step S1, providing compounds A and B with the following structural formulas:

[0044] Compound A is That is, 3,7-dibromodibenzothiophene sulfone;

[0045] Compound B is (i.e., (10-arylanthracen-9-yl)boronic acid) or (i.e., (10-arylanthracen-9-yl)boronate)

[0046] In compound B, Ar- is an aromatic group, and the aromatic group is any one of the following structural formulas:

[0047]

[0048] Step S2, in an inert gas atmosphere (including a protective gas composed of nitrogen or argon), dissolve compounds A and B in an organic solvent containing a catalyst and a lye in a molar ratio of 1:2 to 1:3, and dissolve them at 60 to Carry out Suzuki reaction at 130°C for 8-48 hours, and the obtained structural formula is The described dibenzothiophene sulfone-containing organic semico...

Embodiment 1

[0058] This embodiment discloses an organic semiconductor material containing dibenzothiophene sulfone, that is, 3,7-bis(10-phenylanthracene-9-yl)dibenzothiophene sulfone (DPAFSO), the structural formula is as follows:

[0059]

[0060] Among them, Ar- is

[0061] Step 1, the preparation of 3,7-dibromodibenzothiophene sulfone:

[0062]

[0063] Dissolve 4 mmol of dibenzothiophene sulfone in 30 ml of concentrated H 2 SO 4 8.2mmol NBS was added at room temperature, and after stirring for 24h, the reaction solution was poured into water, filtered with suction, and washed with water and methanol. The remaining solid was recrystallized from chlorobenzene to give 3,7-dibromodibenzothiophene sulfone as a colorless needle solid. Yield: 49%. MS: m / z 374 (M + ).

[0064] Step 2, preparation of 3,7-bis(10-phenylanthracene-9-yl)dibenzothiophene sulfone (DPAFSO):

[0065]

[0066] Add 3,7-dibromodibenzothiophene sulfone 3mmol, 10-(phenylanthracene-9-boronic acid) 6.4mmol,...

Embodiment 2

[0069] This embodiment discloses an organic semiconductor material containing dibenzothiophene sulfone, that is, 3,7-bis(10-(4-methoxyphenyl)anthracene-9-yl)dibenzothiophene sulfone (DMOPAFSO), whose structural formula is as follows:

[0070]

[0071] Among them, Ar- is

[0072] Step 1: same as step 1 of embodiment 1;

[0073] Step 2: Preparation of 3,7-bis(10-(4-methoxyphenyl)anthracen-9-yl)dibenzothiophene sulfone (DMOPAFSO):

[0074]

[0075] Add 3,7-dibromodibenzothiophene sulfone 3mmol, 10-(4-methoxyphenyl)anthracene-9-boronate 6.5mmol, tetrakistriphenylphosphine palladium 0.09mmol into the reaction flask, pump After vacuum and nitrogen circulation for 3 times, the reaction system was in an oxygen-free state. Under the protection of nitrogen, 50 mL of ethylene glycol dimethyl ether and 2 mol / L of Cs were added. 2 CO 3 Aqueous solution 34ml, the mixture was heated to 75-80 ℃ reflux reaction for 24h.

[0076] After the reaction, the reaction solution was poured ...

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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses an organic semiconductor material containing dibenzothiophene sulfone, and a preparation method and an application thereof. The organic semiconductor material has a general formula of (I). In the formula, Ar- is aromatic group. According to the invention, through interactions and mutual influences of anthryl, dibenzothiophene sulfone, and substituted aryl units, the organic semiconductor material containing dibenzothiophene sulfone unit has excellent carrier transportation performance and thermal stability. With the existences of dibenzothiophene sulfone and electron withdrawing groups such as fluorine group, cyano group, aldehyde group, or nitro group, the organic semiconductor material containing naphthalene, anthracene, and dibenzothiophene sulfone units has relatively high electron mobility. When a luminescent layer prepared by using the organic semiconductor material is used in an organic luminescent device, charge balance of the luminescent layer can be promoted, such that luminous efficiency of the organic electroluminescent device can be improved.

Description

technical field [0001] The invention relates to organic semiconductor materials, in particular to an organic semiconductor material containing dibenzothiophene sulfone. The invention also relates to the preparation method and application of the dibenzothiophene sulfone-containing organic semiconductor material. Background technique [0002] With the development of the information age, organic electroluminescent flat panel displays (OLEDs) with high efficiency, energy saving and light weight and large-area white light illumination have attracted more and more attention. OLED technology has attracted the attention of scientists around the world, and related companies and laboratories are conducting research and development of this technology. As a new type of LED technology, organic electroluminescent devices with the characteristics of active light emission, lightness, thinness, good contrast, low energy consumption, and flexible devices can put forward higher requirements f...

Claims

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Application Information

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IPC IPC(8): C07D333/76H01L51/54
Inventor 周明杰王平梁禄生张振华
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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