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A kind of pyrene-based organic semiconductor laser material and its preparation method and application

A technology of organic semiconductors and laser materials, applied in the field of pyrene-based organic semiconductor laser materials and their preparation, can solve the problems of effective control of electrical properties, high threshold value of optical gain medium, complex material preparation, etc., and achieve excellent thermal stability, preparation method Simple, Inexpensive Effects

Active Publication Date: 2019-06-07
NANJING UNIV OF POSTS & TELECOMM
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Problems solved by technology

[0004] Technical problem: The present invention provides a pyrene-based organic semiconductor laser material and its preparation method and application to solve the current problems of high threshold of optical gain medium, poor stability, poor electrical performance, and complicated material preparation, and to overcome the problems of organic semiconductor laser materials in The problem of effective regulation of electrical properties while ensuring excellent photophysical properties

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  • A kind of pyrene-based organic semiconductor laser material and its preparation method and application
  • A kind of pyrene-based organic semiconductor laser material and its preparation method and application
  • A kind of pyrene-based organic semiconductor laser material and its preparation method and application

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preparation example Construction

[0024] The preparation method of the present invention comprises: chemically reacting diphenylamine with 2,7-dibromofluorene to obtain a monobromo-substituted derivative of fluorene modified with a unilateral diphenylamine end group, then carrying out a boron esterification reaction, and finally combining it with pyrene Tetrabromonucleus was prepared by Suzuki coupling reaction to obtain compound P n F. This kind of four-substituted butterfly-shaped organic semiconductor laser material based on diphenylamine terminal group modification with pyrene as the core and fluorene chain as the arm has low threshold, high optical gain coefficient, high thermal stability and excellent electroluminescence performance. It has the following general structural formula:

[0025]

[0026] Wherein, R is a C1-C30 linear or branched alkyl or alkoxy group; n is a natural number of 1-5; N is a nitrogen atom; H ​​is a hydrogen atom.

[0027] More specifically, said R may be one of methyl, ethy...

Embodiment 1

[0033]

[0034] Reaction condition one: in N 2 Under protective conditions, diphenylamine (169.1mg, 1mmol), 9,9-dihexyl-2,7-dibromofluorene (980.2mg, 2.0mmol), potassium tert-butoxide (179.5mg, 1.6mmol), iodide Cuprous catalyst (9.5mg, 0.05mmol) and phase transfer catalyst (0.5mL) was dissolved in 80mL of anhydrous 1,4-dioxane solution, under the condition of temperature control at 110°C, protected from light with tinfoil, reacted for 48h; after the reaction was completed, cooled to room temperature, extracted and purified by chromatographic column to obtain the reaction Product 2a (324.9 mg), yield 56.1%.

[0035] Reaction condition two: in N 2 Under protective conditions, diphenylamine (169.1mg, 1mmol), 9,9-dihexyl-2,7-dibromofluorene (1.2g, 2.5mmol), potassium tert-butoxide (202.1mg, 1.8mmol), iodide Cuprous catalyst (11.4mg, 0.06mmol) and phase transfer catalyst (0.4mL) was dissolved in 80mL of anhydrous 1,4-dioxane solution, under the condition of temperature con...

Embodiment 2

[0039]

[0040] Reaction condition one: in N 2 Under protective conditions, the reaction product 2a (5.8g, 10mmol) was dissolved in 80mL of tetrahydrofuran solvent that had been dried by bubbling, and the reaction device was placed in an ice-water bath (acetone+dry ice) at -78°C, and 7.8mL of n-C 4 h 9 Li is added to the reaction device in small amounts several times; the n-C 4 h 9 After all the Li was injected (1.5h), 4.5mL of isopropanol pinacol borate was added; under temperature control at 0°C, the reaction was carried out for 12h; after the reaction was completed, it was cooled to room temperature and purified by extraction and chromatographic column to obtain the reaction product 3a ( 2.5 g), yield 40.1%.

[0041] Reaction condition two: in N 2 Under protective conditions, the reaction product 2a (8.7g, 15mmol) was dissolved in 85mL of tetrahydrofuran solvent that had been bubbled and dried, and the reaction device was placed in an ice-water bath (acetone+dry ice...

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Abstract

The invention discloses a pyrene-based organic semiconductor laser material and its preparation method and application. The material uses pyrene as the core, diphenylamine groups as end-capping units, fluorenyl groups with different chain lengths as bridging units, and four-substitution symmetry. Pyrene is a butterfly structure of the core, and the material has a general structural formula as shown in the following formula: wherein, R is a C1-C30 linear or branched chain alkyl or alkoxy group; n is a natural number of 1-5. The material of the present invention is simple to prepare, the intermediate cost is low, the reaction process is easy to control, the product is easy to separate, the yield is high, and the purity is high; the material not only shows good thermal stability, low threshold value, and low water content in organic laser devices Oxygen sensitivity and high luminous intensity, and exhibit ultra-low turn-on voltage, excellent luminous brightness and efficiency in organic electroluminescent devices; show important application potential in organic semiconductor laser devices and organic electroluminescent devices .

Description

technical field [0001] The invention belongs to the technical field of optoelectronic materials, and in particular relates to a pyrene-based organic semiconductor laser material and its preparation method and application. 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 optoelectronics research. In recent years, research on organic semiconductor lasers with compact structure and low price (even disposable) has aroused people's great interest. Compared with dye lasers, organic semiconductor materials not only have the advantages of organic laser dyes (high luminous efficiency, wide tunable spect...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/61C07C209/68C09K11/06H01L51/54
CPCC09K11/06C07C209/10C07C209/68C07C211/61C07F5/02C09K2211/1014H10K85/633
Inventor 赖文勇张浩吕鹏李祥春黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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