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Fully-conjugated spiral fused ring trapezoidal organic molecule as well as preparation method and application thereof

A technology of organic molecules and fused rings, applied in organic chemistry, chemical instruments and methods, preparation of amino compounds from amines, etc., can solve the problems of lack of organic nonlinear optical material systems, poor photothermal stability, lack of species, etc. Effects of laser thermal stability, luminescence stability, and high laser gain characteristics

Pending Publication Date: 2021-07-23
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

It effectively solves the technical problems of the current organic laser gain medium material system, such as the lack of material types, poor photothermal stability, low gain, and high threshold. It is a class of organic light-emitting / laser materials with important application potential.
The extremely high multiphoton absorption cross-section of the material system is conducive to solving the problem of the shortage of organic nonlinear optical material systems, and has broad application prospects in the fields of nonlinear luminescence and lasers as an up-conversion luminescent material

Method used

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  • Fully-conjugated spiral fused ring trapezoidal organic molecule as well as preparation method and application thereof
  • Fully-conjugated spiral fused ring trapezoidal organic molecule as well as preparation method and application thereof
  • Fully-conjugated spiral fused ring trapezoidal organic molecule as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1: Realize the synthesis of precursor 1, 2, 3

[0053] We start from simple raw materials to synthesize target precursors 1, 2, 3, such as the reaction scheme Figure 1 . Among them, step (I) realizes Friedel-Crafts acylation and Friedel-Crafts alkylation reaction through terebromophthalic acid to obtain important monomer 4; step (II) carries out Suzuki coupling reaction through important monomer 4 and triphenylamine borate Precursor 1 is obtained; Step (III) realizes Ullmann's Ullman under the condition of 100°C by using raw materials 2,7-dibromomethylfluorene and diphenylamine under the action of sodium tert-butoxide and L-proline and dioxane as solvent. Coupling reaction obtains monomer 5; Step (IV) obtains its borate monomer 6 by monomer 5 through diboronic acid pinacol ester, divalent palladium catalysis, dioxane solvent conditions; Step (V) Carry out Suzuki coupling reaction by monomer 6 and important monomer 4 to obtain precursor 2; Step (VI) obtain ...

Embodiment 2

[0056] Embodiment 2: the synthesis of compound A

[0057]

[0058] 【Reaction route Figure II 】Such as Figure 19 shown.

[0059]

[0060] According to the reaction scheme, tetrabromospirofluorene is obtained through diboronic acid pinacol ester, divalent palladium catalysis, and dioxane solvent to obtain spirofluorene tetraborate monomer; spirofluorene tetraborate, precursor 1 The four-arm spirofluorene precursor was obtained by Suzuki coupling reaction; the lithiation of bromobutylbenzene was realized by butyl lithium, and the lithium butylbenzene attacked the carbonyl active site, and finally the cyclization process was realized by boron trifluoride ether. The specific experimental process is as follows:

[0061] Step i: Under nitrogen, 2,2',7,7'-tetrabromospirofluorene (1.26g, 2.0mmol), biboronic acid pinacol ester (3.05 g, 12.0mmol), potassium acetate (1.88g , 18.0mmol) and 1,4-dioxane (30mL) were added to a 100mL reaction flask, followed by the addition of Pd (...

Embodiment 3

[0065] Embodiment 3: the synthesis of compound B

[0066]

[0067] 【Reaction route Figure three 】Such as Figure 20 shown.

[0068]

[0069] The synthesis method of compound B is similar to the synthesis method of compound A.

[0070] 1 H NMR (400MHz, CDCl 3 ,δ):7.66(s,4H),7.60(d,J=5.5Hz,8H),7.51(d,J=12.9Hz,8H),7.46(d,J=8.3Hz,4H),7.27(s ,4H),7.25(d,J=2.5Hz,8H),7.21(d,J=7.6Hz,12H),7.11(d,J=16.1Hz,56H),7.03–6.87(m,36H),2.68 –2.59(m,16H),2.43(d,J=8.2Hz,16H),1.72–1.63(m,16H),1.50–1.39(m,56H),1.27(t,J=7.2Hz,16H), 0.99(t,J=7.3Hz,24H),0.83(t,J=7.3Hz,24H). 13 C NMR (100MHz, CDCl 3 ,δ):155.44,152.98,152.17,151.94,151.76,151.72,148.89,148.22,148.00,146.99,143.74,143.65,141.80,140.84,140.71,140.61,140.07,139.80,139.03,138.49,134.54,129.17,128.75, 128.35,128.16,128.06,123.89,123.55,122.47,120.51,118.86,117.77,117.30,117.15,116.80,114.02,64.63, 64.38,64.35,46.48,35.54,35.30,33.71,33.52,27.35,22.76,22.51,14.09, 13.95. MALDI-TOF MS(m / z): calcd for C 325 h 308 N 4 ,exact m...

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Abstract

The invention relates to a fully-conjugated spiral fused ring trapezoidal organic molecule as well as a preparation method and application thereof. The material is a spiral fused ring trapezoidal organic molecular compound which takes spirofluorene as a core and trapezoidal fluorene as an arm and is capped with diphenylamine. The material system is clear in chemical structure, high in purity, good in thermal stability and high in glass transition temperature, and can easily form a uniform amorphous film; meanwhile, the material system has high fluorescence quantum efficiency, good photo-thermal stability and extremely high multi-photon absorption cross section; the material has an important application potential in the fields of organic electroluminescent devices, organic laser devices, organic nonlinear optics, organic field effect transistors, perovskite organic-inorganic hybrid solar cells and the like; and particularly, the material has important application value for realizing organic electric pumping laser and LED pumping laser.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials and applications, and relates to a fully conjugated spiro-condensed ring trapezoidal organic molecule and its preparation method and application. The material system can be used as an organic luminescent gain medium for optically pumped organic lasers and electrically pumped organic laser devices; it can be used as an up-conversion luminescent body for nonlinear luminescence and lasers; it can also be used as an organic luminescent material for organic electroluminescence devices; and as a hole transport material used in perovskite organic-inorganic hybrid solar cells, etc. 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C209/68C09K11/06H01L51/46H01L51/42H01L51/54H01L51/50
CPCC07C211/61C09K11/06C09K2211/1011C09K2211/1007C07C2603/97H10K85/625H10K85/633Y02E10/549
Inventor 赖文勇江翼黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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