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Polyspirofluorene containing hole transport group on side chain and preparation method and application thereof

A hole-transporting group, polyspirofluorene technology, used in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve the problems of device performance degradation, unfavorable PLED, damage to interface surface morphology, etc., and achieve low startup. Voltage, Effects of High Device Efficiency

Inactive Publication Date: 2018-09-28
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the addition of the hole transport layer increases the complexity of device fabrication, which is not conducive to the preparation of large-area PLEDs, and when solution processing multilayer organic layer devices, it is easy to cause interlayer mutual dissolution, which destroys the surface morphology of the interface, resulting in Device performance degradation

Method used

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  • Polyspirofluorene containing hole transport group on side chain and preparation method and application thereof
  • Polyspirofluorene containing hole transport group on side chain and preparation method and application thereof
  • Polyspirofluorene containing hole transport group on side chain and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] This embodiment provides a side chain containing polyspirofluorene P(C 8 The preparation method of TPA-SF).

[0036] (1) Preparation of 4-bromo-N,N-di(4-octylphenyl)aniline

[0037] Weigh 1-iodo-4-N-octylbenzene (22g, 70mmol), 4-bromoaniline (5.16g, 30mmol), 1,10-phenanthroline (0.632g, 3.5mmol), cuprous iodide ( 0.636g, 3.5mmol), potassium hydroxide (0.7mol, 39.2g) in a 250ml single-necked bottle, then add 84ml xylene and 56ml toluene. Under the protection of freezing liquid (absolute ethanol at about -40°C), the argon gas was changed three times, heated to 135°C, and refluxed for 24 hours. Cool down to room temperature, spread a layer of silica gel on a sand core funnel for suction filtration, and wash the filter cake three times with dichloromethane. Spin dry, pump dry, weigh, dissolve with dichloromethane, add 1 to 2 times of silica gel, spin dry, purify by silica gel chromatography, spin dry, pump dry, finally get 6.8g of colorless liquid product, yield = 41%. ...

Embodiment 2

[0069] This embodiment provides a method for preparing polyspirofluorene sPF whose side chain does not contain hole transport groups.

[0070] (1) Preparation of 2,7-dibromo-2'-(2-ethylhexyloxy)-9,9'-spirobifluorene

[0071] Weigh 2-bromo-4'-((2-ethylhexyl)oxy)-1,1'-biphenyl (4.33g, 12mmol) in a 250ml three-necked flask, change argon three times, inject 150ml of dried THF was dissolved, cooled to -78°C, and n-butyl lithium (7.5ml, 18.75mmol) was injected into the constant pressure dropping funnel, and added dropwise slowly. Reacted at -78°C for 2h, weighed dibromofluorenone (4.1g, 12mmol), quickly added it into a three-neck flask, reacted at about -60°C for 2h, raised the temperature naturally, and stirred overnight. The next day, 10 g of ammonium chloride and 100 ml of water were added to the reaction solution to quench it. Extracted three times with ethyl acetate, combined organic layers, washed with water, washed with saturated brine, dried over anhydrous magnesium sulfat...

Embodiment 3

[0087] This embodiment provides the polyspirofluorene P(C 8 TPA-SF) and the comparative application of the sPF prepared in Example 2 without a hole-transporting group in the side chain in an electroluminescent device.

[0088] Based on polymer P(C 8 Preparation of electroluminescent devices of TPA-SF) and sPF

[0089] The pre-made indium tin oxide (ITO) glass with a square resistance of ≤12Ω / mouth is ultrasonically cleaned with deionized water, acetone, detergent, deionized water and isopropanol for 20 minutes, and placed in an oven at 80°C. , dry overnight. Treat with oxygen plasma for 4 minutes before use; Spin-coat PEDOT:PSS on ITO, spin-coating speed is 3000r, 30s, and the thickness is about 40nm. After the spin coating is finished, place it on a heating platform at 120° C. for annealing for 20 min to remove the solvent; then add 16 mg / ml of P(C 8 TPA-SF) xylene solution, or a mixed solution of 16mg / ml sPF xylene and tetrahydrofuran, spin-coated on PEDOT:PSS, with a th...

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Abstract

The invention belongs to the technical field of preparation of organic light-emitting materials, and particularly relates to polyspirofluorene containing a hole transport group on a side chain and a preparation method and the application thereof. The side chain of the polyspirofluorene contains the hole transport group, so that the HOMO energy level of the polyspirofluorene can be increased, the hole injection barrier can be reduced, and achievement of the balance of hole injection and electron injection is facilitated; in addition, the polyspirofluorene light-emitting material has relativelygood solubility, and after the polyspirofluorene light-emitting material is dissolved by a common organic solvent, a film can be formed through spin coating, inkjet printing or printing and a light-emitting layer of a light-emitting diode is prepared; when the light-emitting layer based on the polymer is used for preparing a light-emitting device, the addition of a hole transport layer is not required, so that a preparation technology of the device is simpler; the polyspirofluorene light-emitting material is applied to a single-layer electroluminescent device, the maximum current efficiency (LEmax) thereof is 0.67cd / A, the maximum luminance (Lmax) of the device is 3484cd / m<2>, and the turn-on voltage (Von) of the device is only 2.7v.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic light-emitting materials, and in particular relates to a polyspirofluorene whose side chain contains a hole-transporting group, a preparation method and application thereof. Background technique [0002] In 1990, scientists at the University of Cambridge introduced conjugated polymer poly-p-phenylene vinylene (PPV) into organic electroluminescent devices, pioneering the research on polymer organic light-emitting diodes. Polymer light-emitting diodes have attracted extensive attention from academia and industry because of their advantages such as solution processing, high material utilization, low cost, and large-area preparation. Application prospects. Whether used for full-color display or white light illumination, polymer light-emitting diodes have the advantages of high stability, high color purity and high efficiency of red, blue and green three primary colors. However, compar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02H01L51/50H01L51/54H01L51/46H01L51/42
CPCC08G61/02C08G2261/95C08G2261/94C08G2261/91C08G2261/411C08G2261/5222C08G2261/18C08G2261/3142C08G2261/1412C08G2261/143C08G2261/1424C08G2261/11H10K85/111H10K30/00H10K50/00H10K50/15Y02E10/549
Inventor 莫越奇晋光荣
Owner SOUTH CHINA UNIV OF TECH
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