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Organic semiconductor laser material and preparation method and application thereof

A technology of organic semiconductor and laser materials, which is applied in the field of organic semiconductor laser materials and its preparation, and can solve the problems of large multi-photon absorption cross section

Inactive Publication Date: 2017-08-18
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The results show that this kind of material realizes multi-photon lasing from two-photon to five-photon respectively, and the multi-photon absorption cross-section is larger, which is related to the rigid planar structure of trapezoidal materials. Therefore, trapezoidal materials have important application potential in the field of lasers , but ladder-conjugated molecules with hi-modified receptor structures have not been reported

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Synthesis of Precursor 1, Precursor 2, and Precursor 3

[0043]

[0044] Step 1: add terebromophthalic acid (12.00g, 36.9mmol) into a 250ml reaction flask, and add 150ml thionyl chloride SOCl 2 , under the condition of nitrogen protection, reflux at 85°C for 12 hours. Thionyl chloride was removed, and butylbenzene (17.1mL, 110.9mmol), aluminum chloride AlCl 3 (7.41g, 55.7mmol), 150mL dichloromethane, react at room temperature for 2 hours. After the reaction, extract with dichloromethane and water, collect the organic phase, dry with anhydrous magnesium sulfate, filter with suction, distill off the solvent to get the solid obtained by chromatographic column purification to obtain intermediate 1 (14.76g, yield 72%);

[0045] The second step: under the protection of light and nitrogen, intermediate 1 (3.0g, 5.4mmol), triphenylamine borate (290.1mg, 1.8mmol), tetrakistriphenylphosphine palladium Pd (PPh 3 ) 4 (103.5mg, 0.09mmol), phase transfer catalyst tet...

Embodiment 2

[0054] Precursor 1, Precursor 2 and Precursor 3 of Example 1 were used to prepare the following compound A, compound B, compound C, compound D, compound E and compound F.

[0055]

[0056] Wherein, the synthetic route is as follows respectively:

[0057] Reaction route one

[0058]

[0059] Reaction route two

[0060]

[0061] Reaction route three

[0062]

[0063] Reaction route four

[0064]

[0065] Reaction route five

[0066]

[0067] Reaction route six

[0068]

[0069] Since the synthetic methods of Compound A, Compound B, Compound C, Compound D, Compound E, and Compound F are the same, this embodiment takes the synthesis of Compound A as an example, and the specific steps are as follows:

[0070] Step 1, under the conditions of protecting from light and nitrogen, the precursor 1 (300mg, 0.42mmol), 4-fluorophenylboronic acid (117.6mg, 0.84mmol), tetrabutylammonium bromide (65mg, 0.21mmol), four Triphenylphosphinepalladium (24.1mg, 0.02mmol), NaH...

Embodiment 3

[0078] Example 3 Preparation of Organic Laser Devices

[0079] Toluene was used as the solvent, and any one of Compound A, Compound B, Compound C, Compound D, Compound E, and Compound F was used as the light-emitting host to prepare a 20 mg / mL solution. The quartz plate is ultrasonically cleaned, and the organic laser device is prepared by spin coating. The spin coating condition is 2000rpm, and the film thickness is about 100nm. Among them, the emission peaks of the PL spectra of compounds A / B / C / D / E / F are 427nm / 444nm / 465nm / 437nm / 457nm / 472nm, respectively. With the increase of the conjugation length, the PL emission peaks gradually red shift. ASE peaks are at 430nm / 450nm / 468nm / 447nm / 459nm / 474nm; FWHM are 4.5nm / 4.5nm / 5.1nm / 5.1nm / 4.9nm / 6.1nm; ASE threshold is 4.95μJ / cm 2 , 3.49μJ / cm 2 、3.18μJ / cm 2 , 4.12μJ / cm 2 、3.47μJ / cm 2 , 1.97μJ / cm 2 . The optical gain parameters of the light-emitting subject have a certain range of changes with the laser energy, and the maximum gain ...

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Abstract

The invention relates to an organic semiconductor laser material and a preparation method and application thereof. The organic semiconductor laser material uses a trapezoidal fluorene structure as a skeleton, a trapezoidal linear micromolecule compound which is terminated by different electron receptor units is selected, and the formulas are shown in 2L, 3L or 4L, wherein R is an aryl group; A is an electron receptor structure-modified unit; D is an electron donor structure-modified unit. The organic semiconductor laser material has the advantages that the preparation is simple, the purifying is easy, the chemical structure is clear, the heat stability is better, the glass-transition temperature is high, the reversible electrochemical oxidization reduction characteristic is realized, a uniform non-shaping thin film is easily formed, and the like; the material can adopt the simple solution film forming type to prepare a thin film device, the good heat stability, high laser grain and low laser threshold value are realized in an organic laser device, and the important application value is realized in the organic electric pumping laser and LED (light emitting diode) pumping laser.

Description

technical field [0001] The invention belongs to the technical field of optoelectronic materials and applications, and in particular relates to an organic semiconductor laser material and its preparation method and application. Background technique [0002] π-conjugated organic semiconductor materials are widely used in organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), organic solar cells (OPVs) and organic lasers (Organic Lasers) due to their excellent photoelectric properties, easy synthesis, and solution processing properties. ) and other fields are becoming more and more popular. As a new field of development, organic lasers are relatively backward in development, so researchers focus on the research of optically pumped organic lasers with different feedback structures. In order to achieve electrically pumped organic lasers, the gain medium must have a high current density, which is conducive to the formation of a large number of excitons. ...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07C209/68C09K11/06H01L51/54
CPCC09K11/06C07C45/46C07C209/68C07C211/61C07C221/00C09K2211/1014H10K85/624H10K85/623H10K85/636C07C225/22C07C49/813
Inventor 赖文勇黄维方媚黄津津
Owner NANJING UNIV OF POSTS & TELECOMM
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