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Star-like amphiphilic conjugated molecule material, and preparation method and application thereof

A conjugated molecule and amphiphilic technology, which is applied in luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problems of complex structure of organic light-emitting diode devices and difficult processing of electron injection layer solution, and achieve effective The effect of cathode interface modification, excellent luminous brightness, and efficient blue light emission

Active Publication Date: 2017-12-08
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Technical problem: The object of the present invention is a star-shaped amphiphilic conjugated molecular material and its preparation method and application, so as to avoid the interface erosion phenomenon when the solution method is used to prepare multilayer devices, and to overcome the current solution processing of organic light-emitting diode devices Complex structure, difficulty in solution processing of electron injection layer, etc.

Method used

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  • Star-like amphiphilic conjugated molecule material, and preparation method and application thereof
  • Star-like amphiphilic conjugated molecule material, and preparation method and application thereof
  • Star-like amphiphilic conjugated molecule material, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] The synthetic route is as follows:

[0067]

[0068] Specific steps are as follows:

[0069] Step Ⅰ: 2,7-dibromofluorene (20g, 61.7mmol), 1,6-dibromohexane (35.5mL, 246.9mmol), tetrabutylammonium bromide (TBAB) (2g) add 50g of quality The concentration is 50% potassium hydroxide aqueous solution, react overnight at 65°C. Extracted, spin-dried, and passed through the column at 100-200 meshes to obtain 32 g of compound A with a yield of 160%.

[0070] The second step: Compound A (1g, 1.54mmol), 1-boronic acid ester pyrene (0.421g, 1.28mmol) added tetrabutylammonium bromide (TBAB) (0.099g, 0.31mmol) after pumping nitrogen three times, pumping Nitrogen, avoid light and add catalyst Pd(PPh 3 ) 4 (0.089g, 0.077mmol) was dissolved in 21mL of toluene and 7mL of potassium carbonate aqueous solution, and reacted at 95°C for 12 hours. DCM was extracted and spin-dried to pass through the column to obtain compound B with a yield of 76%.

[0071] Step III: Add compound B (0....

Embodiment 2

[0081] The synthetic route is:

[0082]

[0083] Specific steps are as follows:

[0084] Step Ⅰ: 2,7-dibromofluorenone (30.3g, 89.65mmol) was placed in a 500mL three-necked flask, and phenol (71mL, 591.18mmol), 20mL of methanesulfonic acid, and 120mL of CCl were added 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 the powder was about 28 g of pure white compound C, the yield was 93%.

[0085] The second step: compound C (10g, 19.67mmol), 1,6-dibromohexane (19.20g, 78.71mmol), tetrabutyl ammonium olfactory ammonium (TBAB) (2g) add 50% 50% potassium hydroxide aqueous solution , react overnight at 65°C. Extract, spin dry, and pass through the column with 100-200 mesh. 13.2 g of compound D was obtained, ...

Embodiment 3

[0097] Fabrication of organic light-emitting diodes.

[0098] 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 TPA-FEP / PH-FEP / TPA-OEP / PH-OEP 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.

[0099] The following is a comparison of the electroluminescent performance of the above three single-layer organic light-emitting diode devices:

[0100]

[0101] a The turn-on voltage is defined as a brightness of 1cdm -2 when the working voltage. b at maximum brightness.

[0102] All four single-layer devices use star-like amphiphilic conjugated molecules as both emitter and cathode interface layers. Analyzing the device performance in the table, the current efficiency of device A based on material T...

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Abstract

The invention relates to a star-like amphiphilic conjugated molecule material, and a preparation method and application thereof. The material adopts a fluorene structure as a skeleton, pyrene as a capping group and phosphonate as a polar side group and selects different alkyl chains, and the obtained star-like amphiphilic conjugated molecule compound has a structural general formula as shown in the following formula I: (the formula I is as shown in the specification), wherein R is one of alkyl, alkoxy, alkylphenyl and alkyl phenyl with phosphate; Ar is one of benzene, triphenylamine and tri-indene. The material has the advantages of simple chemical structure, low synthesis cost and the like, has high solution processability, film-forming property and multifunctional optical-electrical characteristic, and can realize high-brightness blue light emitting and efficient cathode interface modification functions simultaneously. An organic light-emitting diode which takes the material as a light-emitting layer and an interface modification layer simultaneously can realize excellent optical-electric characteristic through a simplified device structure and solves the technical problem that high-performance multi-layer devices are processed and manufactured by the solution.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials and applications, and in particular relates to a star-shaped 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 fabrication a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40C07F9/6561C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F9/4018C07F9/4059C07F9/4062C07F9/4075C07F9/6561C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1014H10K85/649H10K85/622H10K85/626H10K85/6572H10K50/17H10K50/11
Inventor 赖文勇黄维王梦一
Owner NANJING UNIV OF POSTS & TELECOMM
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