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Luminescent material having aggregation-induced emission, method of making and application thereof

A technology of aggregation-induced luminescence and luminescence materials, applied in the field of solid-state luminescence materials, can solve problems such as limited application of luminescence materials, and achieve the effect of low light loss coefficient

Active Publication Date: 2015-09-02
HKUST SHENZHEN RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a luminescent material with aggregation-induced luminescent properties and its preparation method and application, to solve the problem of limited application of luminescent materials with aggregation-induced luminescent properties in the prior art

Method used

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  • Luminescent material having aggregation-induced emission, method of making and application thereof
  • Luminescent material having aggregation-induced emission, method of making and application thereof
  • Luminescent material having aggregation-induced emission, method of making and application thereof

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Effect test

Embodiment 1

[0064] Embodiment 1: Synthesis of TPE-Bar

[0065] Structural formula:

[0066]

[0067]Chinese chemical name: 5-(4-(1,2,2-triphenylethenyl)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

[0068] English chemical formula: 5-(4-(1,2,2-triphenylvinyl)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

[0069] Synthetic method: Mix 4-(1,2,2-triphenylvinyl)benzaldehyde 1 (500mg, 1.39mmol) and barbituric acid 3 (186mg, 1.46mmol) in a mixed solvent of methanol 20mL and THF 5mL After reflux for 24 hours, a bright yellow precipitate was formed. After the reaction mixture was cooled to room temperature, the formed bright yellow precipitate was filtered. The filtered solid was washed three times with ethanol and ether, respectively, and dried in vacuo to obtain 390 mg of the product with a yield of 61%. 1 H-NMR (400MHz, d 6 -DMSO): δ11.48(s, 1H), 11.33(s, 1H), 8.26(s, 1H), 8.11(d, J=8.8Hz, 2H), 7.32-7.23(m, 9H), 7.17( d,J=8.4Hz,2H),7.15-7.09(m,6H); 13 C-NMR (100MHz, d 6 -DMSO):163.44...

Embodiment 2

[0070] Embodiment 2: Synthesis of TPE-s-Bar

[0071] Structural formula:

[0072]

[0073] Chinese chemical name: 1,3-dimethyl-5-(4-(1,2,2-triphenylethenyl)benzylidene)pyrimidine-2,4,6(1H,3H,5H)- Triketone

[0074] English chemical formula: 1,3-dimethyl-5-(4-(1,2,2-triphenylvinyl)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

[0075] Synthetic method: Add 4-(1,2,2-triphenylvinyl)benzaldehyde 1 (500mg, 1.39mmol) and N,N-dimethylbarbituric acid 2 (227mg, 1.46mmol) to the mixture A drop of concentrated sulfuric acid was used as a catalyst, and refluxed in ethanol (20mL) for 24h to form an orange-yellow precipitate. After the reaction mixture was cooled to room temperature, the formed orange-yellow precipitate was filtered. The filtered solid was rinsed three times with ethanol and ether, and dried in vacuo. 480 mg of the product was obtained with a yield of 70%. HR-MS (MALDI-TOF) C 33 h 26 N 2 o 3 Theoretical value: 498.1943; Measured value: 498.1941; 1 H-NMR (400MHz,...

Embodiment 3

[0076] Embodiment 3: Synthesis of TPE-HPh-Bar

[0077] Structural formula:

[0078]

[0079] The steps include: (1) synthesizing TPE-HPh

[0080] Chinese chemical name: 2,5-dihexyloxy-4-((4-(1,2,2-triphenylethenyl)phenyl)ethynyl)benzaldehyde

[0081] English chemical formula: 2,5-dihexyloxy-4-((4-(1,2,2-triphenylvinyl)phenyl)ethynyl)benzaldehyde

[0082] Synthetic method: Add 2-(4-ethynylphenyl)-1,1,2-triphenylethenyl 4 (1g, 2.81mmol), 4-bromo-2,5- Dihexyloxybenzaldehyde 6 (1.03g, 2.68mmol), bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh 3 ) 2 Cl 2 ) (0.089g, 0.126mmol), cuprous iodide (0.024g, 0.121mmol) and triphenylphosphine (0.066g, 0.251mmol), the above mixture was vacuumized and gas exchanged three times with nitrogen gas to completely remove oxygen, Pour 30 mL of newly distilled tetrahydrofuran and 10 mL of anhydrous degassed triethylamine into the above-mentioned reaction flask, and react at reflux for 8 hours at 70°C to form a precipitate. After cool...

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Abstract

The invention discloses a luminescent material having aggregation-induced emission, a method of making and an application thereof. The luminescent material herein has properties of aggregation-induced emission (AIE) / aggregation-enhanced emission (AEE) with the maximum absorption wavelength red shift to a visible area so that this type of luminescent material has the potential applications in the field of biology and photoelectricity. The luminescent material herein also has excellent optical waveguide property with an optical loss lower to 0.100dB / [mu]m, and is applicable to produce optical waveguide materials and also applicable to organic light emitting diodes. The luminescent material herein also has the characteristic of mechanochromism and reversible mechanochromism, thus having potential application in the aspect of smart materials.

Description

technical field [0001] The invention relates to a series of organic luminescent materials, in particular to a solid-state luminescent material with characteristics of aggregation-induced luminescence or luminescence enhancement (AIE / AEE). Background technique [0002] With the development of organic optoelectronics, new organic light-emitting semiconductor functional materials used in solid state or aggregated state, due to their high sensitivity, good device flexibility, low cost, small device size, and large area compared with traditional inorganic semiconductor materials Due to the advantages of preparation and easy integration, more and more attention has been paid (Chem. Phys. Lett., 1974, 29, 277, Chem. Rev. 2007, 107, 1011). In addition to organic optoelectronic devices, organic light-emitting materials are used in information storage (J.Mater.Chem.C,2013,1,3376; Chem.Soc.Rev.,2013,42,857; Adv.Mater.,2013,25,378; Chem.Soc. Rev., 2013, 42, 8895.) and biological scienc...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D239/62G02B1/04H01L51/54G01N21/64
Inventor 唐本忠王二静洪煜柠
Owner HKUST SHENZHEN RES INST
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