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Organic semiconductor laser material as well as preparation method and application thereof

A technology of organic semiconductors and laser materials, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of high optical gain medium threshold, complex material preparation, high water and oxygen sensitivity, and achieve high luminous efficiency and migration. efficiency, simple preparation method, and high luminous intensity

Inactive Publication Date: 2015-07-22
NANJING UNIV OF POSTS & TELECOMM
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Problems solved by technology

[0004] Technical problem: The present invention provides a method for preparing a four-substituted butterfly-shaped organic semiconductor laser material based on optical pumping with low threshold, high thermal stability, and low water-oxygen sensitivity, and is easy to prepare. At present, the problems of high threshold value, poor stability and complicated material preparation of optical gain medium have overcome the defects of high water and oxygen sensitivity of organic semiconductor laser materials

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  • Organic semiconductor laser material as well as preparation method and application thereof
  • Organic semiconductor laser material as well as preparation method and application thereof
  • Organic semiconductor laser material as well as preparation method and application thereof

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preparation example Construction

[0029] The preparation method of the present invention comprises: 1-bromopyrene and 2,7-dibromofluorene synthesize the monobromo-substituted derivatives of pyrenylfluorene through Suzuki reaction, then carry out boron esterification reaction, and finally combine it with different four-substituted nuclei Compound I was prepared by Suzuki coupling reaction. The four-substituted butterfly-shaped organic semiconductor laser material based on pyrenylfluorene as the arm has low threshold, low water and oxygen sensitivity and high thermal stability. It has a structure such as formula I:

[0030]

[0031] Wherein, the nucleus A in formula I is one of the following II structures:

[0032]

[0033] Wherein, R is a C1-C20 linear or branched alkyl or alkoxy group; * is a connection position; O is an oxygen atom; N is a nitrogen atom; H ​​is a hydrogen atom.

[0034] The preparation method of the butterfly-shaped organic semiconductor laser material comprises the following steps: ...

Embodiment 1

[0041]

[0042] Reaction condition one: in N 2 Under protection, pyrenyl-1-boronic acid pinacol ester (328.2mg, 1mmol), 9,9-dihexyl-2,7-dibromofluorene (984.6mg, 2mmol) was added to a 150mL reaction flask, and N 2 After three times, Pd(PPh 3 ) 4 Catalyst (57.8mg, 0.05mmol) and phase transfer catalyst TBAB (32.2mg, 0.1mmol) were dissolved in 21mL of toluene and 7mL of K 2 CO 3 In the aqueous solution, the temperature was controlled at 80° C. for 12 hours; after the reaction, the product was purified by chromatographic column to obtain the product of structural formula 1 (343.7 mg), and the yield was 56.1%.

[0043] Reaction condition two: in N 2 Under protection, add pyrenyl-1-boronic acid pinacol ester (328.2mg, 1mmol), 9,9-dihexyl-2,7-dibromofluorene (1.231g, 2.5mmol) into a 150mL reaction flask, and replace N 2 After three times, Pd(PPh 3 ) 4 Catalyst (115.6mg, 0.10mmol) and phase transfer catalyst TBAB (48.3mg, 0.15mmol) were dissolved in 42mL of toluene and 14mL...

Embodiment 2

[0047]

[0048] Reaction condition 1: Under the condition of nitrogen protection, 1-(7-bromo-9,9-dihexyl-9H-fluoren-2-yl)pyrene (613.7mg, 1mmol) and diboronic acid pinacol ester (457.1g, 1.8mmol), Pd(dppf 2 )Cl 2 Catalyst (40.8mg, 0.05mmol) and KOAc (196.0mg, 2mmol) were dissolved in 20mL of anhydrous dioxane solvent, under temperature control at 90°C, and reacted in the dark for 24h; after the reaction was completed, 1-( 7-boronic acid pinacol ester-9,9-dihexyl-9H-fluoren-2-yl)pyrene (366.0 mg), yield 55.4%.

[0049] Reaction condition 2: Under the condition of nitrogen protection, 1-(7-bromo-9,9-dihexyl-9H-fluoren-2-yl)pyrene (613.7mg, 1mmol) and diboronic acid pinacol ester (506.1g, 2.0mmol), Pd(dppf 2 ) Cl 2 Catalyst (81.6mg, 0.10mmol) and KOAc (294.0mg, 3mmol) were dissolved in 35mL of anhydrous dioxane solvent, and the temperature was controlled at 100°C, and reacted in the dark for 30h; after the reaction was completed, 1-( 7-boronic acid pinacol ester-9,9-dihex...

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Abstract

The invention relates to an organic semiconductor laser material as well as a preparation method and an application thereof. The organic semiconductor laser material adopts a butterfly-shaped structure with a pyrene unit as an end sealing unit, fluorenyl as a bridging unit and tetra-substituted symmetric unit as a core, and the material has a structure shown in the specification. The material is simple to prepare, an intermediate is low in cost, a reaction process is easy to control, a product is easy to separate, the yield is high, and the purity is high; the material used for an organic laser device has good thermal stability and film forming stability, low threshold value, low water and oxygen sensitivity and high luminous intensity, and the material has potential application value in the fields of organic semi-conductor laser, organic electroluminescence and organic field effect transistors for electrically pumping due to high lamination efficiency and mobility.

Description

technical field [0001] The invention belongs to the technical field of organic lasers, and in particular relates to a preparation method and application of an organic semiconductor laser material. Background technique [0002] Organic semiconductor materials are widely used in organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), organic solar cells (OPVs) and organic lasers due to their good optical and electrical properties, simple preparation process, and adjustable structure and performance. (Organic Lasers) and other fields have been widely used, and have become an important content of organic electronics research. In recent years, research on organic lasers with compact structure and low price (even disposable) has developed very rapidly. Compared with dye lasers, organic semiconductor materials not only have the advantages of organic laser dyes (high luminous efficiency, wide tunable spectral range, can be regarded as a four-level system, e...

Claims

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Application Information

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IPC IPC(8): C07C13/72C07C13/62C07C1/32C09K11/06
Inventor 赖文勇黄维赵丽易建鹏李祥春闫聪飞
Owner NANJING UNIV OF POSTS & TELECOMM
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