Conjugation arborization electroinduced ethereal blue light material, preparation method and application thereof

A dendritic and conjugated technology, applied in the direction of luminescent materials, chemical instruments and methods, circuits, etc., can solve the problems of insufficient luminous brightness and color purity of blue light materials, restrictions on the development of polyfluorene materials, poor solubility and stability, etc. Achieve the effects of reducing fluorescence quenching, improving efficiency and color purity, and increasing solubility

Inactive Publication Date: 2008-07-16
PEKING UNIV
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Problems solved by technology

And the polymer blue light material that appears at first is polyparaphenylene (PPP), but because solubility and stability are poor, have limited the development of this kind of molecule, subsequently appeared the blue light material of many soluble polyparaphenylene derivatives, but they still poor stability
At the beginning of the emergence of polyfluorene polymer blue light materials, it has received widespread attention. However, due to the long-wavelength emission (in the green light emitting region) of high polyfluorene or oligomeric fluorene materials under electric field conditions, the device The color purity is reduced, which also restricts the development of polyfluorene materials
At the end of the last century, people began to use conjugated dendrimers to prepare blue light materials. Conjugated dendrimers based on 1,2-stilbene are among the better blue light materials. However, such dendrimers are only available in Higher algebra can reduce the formation of exciplexes, which undoubtedly greatly increases the cost of materials. Moreover, the best blue light materials in this type of dendrimers are obviously insufficient in luminous brightness and color purity.

Method used

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  • Conjugation arborization electroinduced ethereal blue light material, preparation method and application thereof
  • Conjugation arborization electroinduced ethereal blue light material, preparation method and application thereof
  • Conjugation arborization electroinduced ethereal blue light material, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1: Preparation of G0 and its property determination

[0055] Horner-Wadsworth-Emmons reaction of the triphosphonate 5 shown below with the monoaldehyde derivative 7 of trisindene affords GO. The synthesis of triphosphonates, monoaldehyde derivatives of tripolyindene and GO is shown below:

[0056]

[0057] (1) Preparation of compounds 2 and 6:

[0058] Under nitrogen protection, 2.21g (1.1eq., 14.72mmol) 4-formylphenylboronic acid, 20g tribromide 1 (1.0eq., 18.40mmol), 10mg Pd(PPh 3 ) 4 Add 75 mL THF and 68 mL 2M Na 2 CO 3 In aqueous solution, reflux for 10 hours. Cool, extract the organic phase, NH 4 Washed with saturated aqueous Cl solution, anhydrous Na 2 SO 4 dry. The solvent was removed under reduced pressure, and the solid was separated through a silica gel column, and the developing solvent was petroleum ether / ethyl acetate=20 / 1~10 / 1 (volume ratio), and yellow solid trialdehyde 2 (9%) and monoaldehyde 6 ( 34%). Trialdehyde 2: 1 H NMR (CD...

Embodiment 2

[0071] Embodiment 2: Preparation of G1 and its property determination

[0072] Next-generation monoaldehydes undergo Horner-Wadsworth-Emmons reactions with triphosphonates to give G1. The synthesis of next-generation monoaldehydes and G1 is shown below:

[0073]

[0074] (1) Preparation of compound 8:

[0075] Dialdehyde 8 was prepared together with trialdehyde 2 and monoaldehyde 6, and the yield of dialdehyde 8 was 23%. 1 HNMR (CDCl 3 , 300MHz, ppm): δ10.11(2H, s), 8.44(2H, m), 8.26(1H, d, J=9.0Hz), 8.03(4H, d, J=8.5Hz), 7.93(4H, d, J=8.5Hz), 7.74-7.72(4H,m), 7.61(1H,s), 7.55(1H,d,J=9.0Hz), 3.04-2.89(6H,m), 2.21-2.05(6H , m), 1.02-0.77 (36H, m), 0.63-0.50 (30H, m). 13 C NMR (CDCl 3 , 75MHz, ppm): δ191.9, 155.9, 154.4, 147.2, 145.9, 145.6, 145.1, 140.5, 139.0, 138.0, 137.9, 137.8, 137.6, 135.1, 131.2, 130.9, 130.3, 129.7, 1289.5, 12 126.6, 126.2, 126.0, 125.6, 125.1, 124.4, 121.4, 121.0, 120.2, 55.9, 37.7, 37.1, 36.8, 36.1, 31.4, 29.4, 23.9, 22.2, 13.8. MALDI-TOF MS ...

Embodiment 3

[0090] Embodiment 3: device making

[0091] The typical device manufacturing process of the present invention is as follows: ITO (indium tin oxide) glass is ultrasonicated for ten minutes with acetone, alkaline washing solution, pure water (twice), and isopropanol, and then treated with ozone plasmar for 5 minutes. The hole injection layer PEDOT (poly(3,4-ethylenedioxythiophene)) was spin-coated on the treated substrate to form a film with a thickness of 50 nm, and was heated in air at 160° C. for 6 minutes. A hole transport layer PVK (poly(9-vinylcarbazole)) (thickness 40 nm) was spin-coated thereon, and heated for 15 minutes in a nitrogen atmosphere. Then spin-coat the light-emitting layer (G0 or G1, thickness 60nm), and heat for 15 minutes in a nitrogen atmosphere. Finally, Ba / Al (with a thickness of 4.5nm / 150nm) is vacuum evaporated to complete the device. The device structure is ITO / PEDOT(50nm) / PVK(40nm) / G0 or G1(60nm) / Ba(4.5nm) / Al(150nm). The starting voltage of the G...

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Abstract

The invention provides a pure blue light material of a conjugated branchlike molecular and an organic electroluminescence device by using the blue light material as an emitting layer. The blue light material of the invention is a conjugated branchlike molecule, which takes a trimeric indene as a nuclear and a trans 1, 2-stilbene as a bridge; the blue light material is obtained through Homer-Wadsworth-Emmons reaction or Wittig reaction of three phosphonate and single-aldehyde derivative of the trimeric indene; conjunction length and molecular weight of the material are rapidly increased, and emission of the pure blue light and film forming capability of the material are correspondingly regulated. Furthermore, the branchlike structure of the material and an replaced alkyl chain effectively reduce molecular aggregation, thereby obtaining high-purity blue light. By using the conjugated branchlike molecular as the emitting layer material of the organic electroluminescence diode device, the organic electroluminescence diode device can be prepared by simple spin coating process and membrane making; the invention can successfully emit the pure light, with good photoelectric stability.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a new class of stable conjugated dendritic molecular materials, which can be used as pure blue light materials in the light-emitting layer of organic electroluminescent diodes (OLEDs). Background technique [0002] In recent years, organic light-emitting diode (OLED) has gradually become an important development direction in the field of flat-panel display. more attention. In OLED devices, holes are injected from the anode and electrons are injected from the cathode under an electric field, and the excitons are recombined in the organic light-emitting layer, and finally the excitons are withdrawn to emit visible light. Generally, good organic light-emitting materials must have high quantum efficiency, good film-forming properties, and excellent optical and electrical stability. OLED light-emitting materials can be divided into two categories according to the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/62C09K11/06H01L51/50H01L51/54
Inventor 裴坚江泱王婕妤马玉国
Owner PEKING UNIV
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