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A kind of multifunctional amphiphilic conjugated molecular material and its preparation method and application

A conjugated molecule and amphiphilic technology, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problems of complex structure, electron injection layer cannot be processed by solution, etc., and achieve low cost, excellent alcohol Solubility, the effect of good solubility

Active Publication Date: 2019-02-26
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Technical problem: The present invention provides a multifunctional amphiphilic conjugated molecular material and its preparation method and application, so as to solve the problems of complex structures of OLED devices in solution processing and the inability to process the electron injection layer in solution.

Method used

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  • A kind of multifunctional amphiphilic conjugated molecular material and its preparation method and application
  • A kind of multifunctional amphiphilic conjugated molecular material and its preparation method and application
  • A kind of multifunctional amphiphilic conjugated molecular material and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: The reaction scheme is as follows.

[0049]

[0050] Specific steps are as follows:

[0051] The first step: 2,7-dibromofluorene (20g, 61.7mmol), 1,6-dibromohexane (35.5mL, 246.9mmol), tetrabutyl ammonium chlorinated ammonium (TBAB) (2g) was added to the quality of 50g Fractions were reacted overnight at 65°C in 50% potassium hydroxide aqueous solution. Extracted, spin-dried, and passed through the column at 100-200 meshes to obtain 32 g of compound A with a yield of 160%.

[0052] Step II: Compound A (6g, 9.23mmol), pinacol borate (9.36g, 36.9mmol) was pumped three times for nitrogen, and then potassium acetate (9.34g, 64.6mmol) was added, nitrogen was pumped, and the catalyst was added in the dark Pd(pddf) 2 Cl 2 (0.4g, 0.524mmol) was dissolved in 45mL of dioxane, and reacted at 100°C for 24h under the protection of nitrogen. Extraction was spin-dried and passed through the column to obtain 4.93 g of compound B with a yield of 82%.

[0053] Step...

Embodiment 2

[0057] Embodiment 2: The reaction scheme is as follows.

[0058]

[0059] Specific steps are as follows:

[0060] Step Ⅰ: 2,7-dibromodifluorenone (30.3g, 89.65mmol) was placed in a 500mL three-necked flask, and phenol (71mL, 591.18mmol), 120mL of CCl 4 , the temperature was adjusted to 80°C, and the reaction was carried out for 42h. Stop the reaction, cool with K 2 CO 3 The solution is quenched, and it should be added slowly, and a large number of bubbles will be generated. After suction filtration, the waste liquid is purple. Washed with DCM several times until about 28 g of compound D was pure white in powder form, with a yield of 93%.

[0061] The second step: Compound D (10g, 19.67mmol), 1,6-dibromohexane (19.20g, 78.71mmol), tetrabutyl ammonium olfactory ammonium (2g) adding 50g mass fraction is 50% potassium hydroxide In aqueous solution, react overnight at 65°C. Extract, spin dry, and pass through the column with 100-200 mesh. 13.2 g of compound E was obtaine...

Embodiment 3

[0068] Fabrication of organic light-emitting diodes.

[0069] OLEDs single-layer devices were prepared by spin-coating method: the device structure was ITO / PEDOT:PSS 35nm / luminescent layer 65nm / Al 80nm. Chloroform was used as a solvent, and any one of the compounds PEP / POEP was used for the light-emitting layer to prepare a 15 mg / mL solution. Spin coating under the protection of nitrogen, the rotating speed is 1500rpm, annealing at 80°C for 10min.

[0070] OLEDs single-layer devices were prepared by inkjet printing: the device structure was ITO / PEDOT:PSS 35nm / PEP / Al80nm. Use ethylene glycol methyl ether as a solution to configure 14mg / mL ink. Anneal at 100°C for 20min.

[0071] The following is a comparison of the electroluminescent performance of the above three single-layer organic light-emitting diode devices:

[0072]

[0073] a Turn-on voltage is defined as a brightness of 1cd m -2 when the working voltage. b at maximum brightness. c Prepared by inkjet printing. ...

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Abstract

The invention discloses a multifunctional amphiphilic conjugated molecular material and its preparation method and application. The material is composed of high-efficiency luminescent fluorene and pyrene substances, phosphonate is used as a polar side group, and different alkyl chains are selected. The linear molecular compound, its general structural formula is shown in the following formula: wherein, R is one of C1-C30 alkyl, alkoxy, alkylphenyl, alkylphenoxy, aryl. The material has the advantages of simple chemical structure and low synthesis cost, as well as good solution processing performance, film-forming performance and multifunctional optoelectronic properties. It can be used as a multifunctional material to simultaneously achieve high-brightness blue light emission and efficient cathode interface modification. Organic light-emitting diodes using this material as both the light-emitting layer and the interface layer can use a simplified device structure to achieve excellent optoelectronic characteristics through solution process or inkjet printing, which overcomes the manufacturing obstacles in conventional multilayer devices.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials and applications, and in particular relates to a multifunctional amphiphilic conjugated molecular material and its preparation method and application. Background technique [0002] Organic light-emitting diodes (OLEDs) have been widely used in fields such as full-color flat-panel displays, solid-state lighting, and large-area flexible electronics. Due to their remarkable progress in materials chemistry and device physics, vacuum-deposited small-molecule OLEDs with multilayer structures have entered commercial applications. However, the manufacturing process of the vacuum deposition method is complicated, the cost is high and the material utilization rate is low. Furthermore, the use of shadow masks limits the scalability and resolution of devices during vapor deposition. In contrast, solution-processed OLEDs have attracted considerable attention for their cost-effective fabricati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/40C09K11/06H01L51/50H01L51/54H01L51/56
CPCC09K11/06C07F9/4006C07F9/4018C09K2211/1011H10K71/12H10K71/135H10K85/622H10K85/626H10K85/615H10K50/171H10K50/11
Inventor 赖文勇黄维王梦一
Owner NANJING UNIV OF POSTS & TELECOMM
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