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Trapezoidal macromolecular derivative, preparation and applications thereof

A technology of macromolecules and derivatives, which is applied in the field of trapezoidal macromolecular derivative materials and its preparation, and can solve problems such as high threshold, poor photothermal stability, and low gain

Active Publication Date: 2017-10-13
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the deficiencies in the prior art, the object of the present invention is to provide a ladder-like macromolecular derivative material and its preparation method and application. The ladder-like macromolecular derivative material is a class of organic laser materials with application potential, which solves the current problems Organic laser gain medium material system lacks material types, poor photothermal stability, low gain, high threshold and other problems

Method used

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  • Trapezoidal macromolecular derivative, preparation and applications thereof
  • Trapezoidal macromolecular derivative, preparation and applications thereof
  • Trapezoidal macromolecular derivative, preparation and applications thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Example 1 Synthesis of Precursor 1, Precursor 2, and Precursor 3

[0040] In the first step, Friedel-Crafts acylation and Friedel-Crafts alkylation reaction of terebromophthalic acid to obtain intermediate 1

[0041] In the second step, intermediate 1 is subjected to Suzuki coupling reaction with triphenylamine borate to obtain precursor 1

[0042] The third step is to realize the Ullman coupling reaction of the raw materials 2,7-dibromomethylfluorene and diphenylamine under the action of sodium tert-butoxide and L-proline under the action of dioxane as a solvent at 100°C to obtain

[0043] Step four, by Obtain its borate monomer under the conditions of pinacol borate, divalent palladium catalysis, and dioxane solvent

[0044] Step five, by Perform Suzuki coupling reaction with intermediate 1 to obtain precursor 2

[0045] The sixth step, from terephthalate and intermediate 1 Suzuki coupling reaction was carried out to obtain intermediate 1

[0046]...

Embodiment 2

[0048] Precursor 1, precursor 2 and precursor 3 of Example 1 were used to prepare compound A

[0049] Compound B

[0050] and compound C Three ladder macromolecular compounds. Wherein, the synthetic route is as follows respectively:

[0051] Reaction route one

[0052]

[0053] Reaction route two

[0054]

[0055] Reaction route three

[0056]

[0057] The synthesis methods of compound A, compound B and compound C are the same, and the synthesis of compound A is taken as an example here, and the specific steps are as follows:

[0058] Step I: Under nitrogen, tribromotriindene (2.2g, 2.0mmol), biboronic acid pinacol ester (2.55g, 10.0mmol), potassium acetate (1.23g, 15.0mmol) and 1,4- Dioxane (40 mL) was added into a 100 mL reaction flask, followed by divalent palladium catalyst (0.30 g, 0.4 mmol), and reacted at 100° C. overnight. The reaction was quenched with ice water, and the organic phase was extracted with dichloromethane, washed two or three times w...

Embodiment 3

[0065] Fabrication of OLED devices

[0066] After the ITO glass is ultrasonically cleaned, it is treated with oxygen plasma, and the square resistance of the ITO glass is 10Ω / cm 2 . The hole injection layer is PEDOT or PVK, and any one of compound A, compound B or compound C is used for the light emitting layer. Both the hole injection layer and the light emitting layer are fabricated by spin coating. Cathode electrode adopts Ca / Al, or Ba / Al metal respectively. Among them, the maximum luminous efficiency of compound A is 0.82cd / A, and the maximum brightness is 776cd / m 2 , CIE coordinates (0.17, 0.18).

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Abstract

The invention relates to a trapezoidal macromolecular derivative, a preparation and applications thereof, wherein the trapezoidal macromolecular derivative is a trapezoidal macromolecular compound by using truxene as a core and using trapezoidal fluorene as an arm and by combining a functional group, R1 and R2 are any one selected from alkyl, alkoxy, alkylphenyl and alkoxyphenyl, and Ar is hydrogen atom, phenyl, 1-naphthyl, 2-naphthyl, phenanthryl, o-phenanthroline, anthryl, 9-phenyl-anthryl, 4-phenylnaphthyl, 2-thienyl, pyridyl, phenyl oxadiazole, pyrenyl, quinolyl, pyridyl, quinazolyl, diphenyltriazolyl, phenylimidazolyl, phenylthiazolyl, phenyloxazolyl, spirobiflourenyl, 9-carbazolyl, 3-(9-phenylcarbazole)yl, diphenylamino, triphenylamino, phenylnaphthylamino, trifluorophenyl, p-fluorophenyl, phenylcyano, cyano or fluoro. According to the present invention, the trapezoidal macromolecular derivative prepared mainly through the Suzuki coupling reaction has advantages of laser gain, laser thermal stability, and ultra low ASE / laser threshold.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials and applications, and in particular relates to a trapezoidal macromolecular derivative material and its preparation method and application. Background technique [0002] π-organic conjugated molecules have great potential in the fields of 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 and ease of processing. more and more widely used. As a new development direction, organic laser is a very important development field of semiconductor laser in the future. In the 1970s, Bell Laboratories in the United States successfully developed heterojunction solid-state lasers, which greatly reduced the threshold current density and opened the door for the application of semiconductor lasers. However, semiconductor lasers manufactured on substrates suc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C209/68C09K11/06
CPCC09K11/06C07C45/46C07C45/68C07C209/10C07C209/68C07C211/61C07C221/00C07F5/02C09K2211/1416C07C49/813C07C225/22Y02B20/00
Inventor 赖文勇黄维江翼常驷驹方媚
Owner NANJING UNIV OF POSTS & TELECOMM
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