Preparation and application of N,N'-di(triphenylamine group) fluorene diamine hole injection material

A technology of hole injection layer and phenyl group, which is applied in the field of N, can solve problems such as the influence of hole injection ability, the high price of PEDOT, the reduction of the barrier between the anode and the hole transport layer, and the driving voltage of the device.

Inactive Publication Date: 2010-03-17
HONG KONG BAPTIST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although they can all achieve the effect of reducing the light-up voltage, the Tg of most of them is lower than 100°C, PEDOT is expensive, and CuPc will absorb red light
2-TNATA has good thermal stability (Tg=110°C) and film-forming properties. Whether it is single or P-type doped as a hole injection material, it can effectively reduce the barrier between the anode and the hole transport layer and the device. Driving voltage, but its hole injection ability is greatly affected by the thickness of the hole injection layer

Method used

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  • Preparation and application of N,N'-di(triphenylamine group) fluorene diamine hole injection material
  • Preparation and application of N,N'-di(triphenylamine group) fluorene diamine hole injection material
  • Preparation and application of N,N'-di(triphenylamine group) fluorene diamine hole injection material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1: BUHI3 described in the present invention can be synthesized by the following method.

[0067] Under nitrogen protection, 2,7-bis[N,N-bis(4-bromophenyl)]amino-9,9-di-n-butylfluorene (1.86g, 2.0mmol) was successively added to a 100mL reaction flask, Diphenylamine (2.04g, 12.0mmol), sodium tert-butoxide (1.54g, 16.0mmol), and 40mL of anhydrous toluene were added after replacing the gas in the reaction flask with inert gas. Under stirring, the pre-prepared Pd(dba) 2 (Di-p-benzylacetone 92mg, 0.16mmol), P(t-Bu) 3 (33 mg of tri-tert-butylphosphonium, 0.16 mmol) in anhydrous toluene (3 mL) was quickly added to the reaction flask, and stirred at 90° C. for 12 h. After the reaction mixture was cooled to room temperature, ammonium chloride solution was added and extracted twice with toluene. The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. Part of the solvent was evaporated under reduced pressure, and the remaini...

Embodiment 2

[0069] BUHI3(CHCl 3 ), F4-TCNQ (CHCl 3 ), BUHI3+F4-TCNQ (CHCl 3 ) UV-Vis see image 3 . For the cyclic voltammetry experiment of BUHI3, see Figure 4 . The highest occupied electron orbital (HOMO) of the host material molecule BUHI3 forming the P-type doping system is 5.07eV, and the lowest unoccupied orbital (LUMO) of the dopant molecule F4-HCNQ is 5.24eV. ​​The energy levels of the two are similar, and the charge transfer occurs. Increased conductivity for hole transport.

Embodiment 3

[0071] This example demonstrates pure hole transport devices fabricated from BUHI3 and BUHI3 doped with F4-TCNQ, respectively. The ITO glass was ultrasonically cleaned in detergent and deionized water successively for 30 minutes. Then vacuum dry for 2 hours (120° C.), then treat the ITO glass with UV / ozone for 25 minutes, and send it to the vacuum chamber to prepare organic film and metal electrode. This experiment includes two devices, the structures are: device 1: ITO / BUHI3(60nm) / Au; device 2: ITO / BUHI3+2%F4-TCNQ(60nm) / Au, where ITO is the square resistance of 10-20 ohms Transparent electrode, BUHI3 is a hole transport semiconductor, and F4-TCNQ is a doping material. Depend on figure 2 It can be seen that after BUHI3 is doped with F4-TCNQ, the device has good hole injection and conductivity, and its current density is two orders of magnitude higher than that of device 1.

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Abstract

The invention relates to an N,N'-di(triphenylamine group) fluorene diamine derivative with a general formula (I), wherein R1 and R2 refer to C1-C20 alkyl, phenyl or benzyl; and R1 and R2 can be same or different. The invention also relates to a method for preparing the compound, application of the compound as a hole injection layer material for an organic electroluminescent device and the organicelectroluminescent device containing the organic hole injection material. The compound is applied to an injection layer of the organic electroluminescent device so as to ensure excellent ohmic contact between the organic material and an electrode, bring convenience to the injection of the hole, improve the transmission efficiency of the hole, lower the driving voltage of the device, improve the efficiency of the device and prevent the thickness of the hole injection material from affecting the performance of the device.

Description

technical field [0001] The present invention relates to N, N'-bis(triphenylamino)fluorene diamine compounds, a preparation method thereof, the use of the compound as a material for the hole injection layer of an organic electroluminescent device, and a compound containing the compound in the hole injection layer Organic electroluminescent devices. Background technique [0002] Organic electroluminescence has attracted the attention of many researchers because of its excellent luminescent properties. In 1987, Deng Qingyun's (Tang, C.W.et Al.Appl.Phys.Lett.1987, 52, 913) research group first proposed the first amorphous OLED. In 1990, Burroughes et al. (Burroughes, J.H. et al. Nature 1990, 347, 539) reported the first polymer light-emitting diode for the first time. Since then, the research on organic electroluminescence has entered a new stage. In recent decades, organic light-emitting diodes with fast response, high brightness, low operating voltage and large area have bee...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54C07C209/06H01L51/50H01L51/54C09K11/06
Inventor 夏萍芳高志强黄文成陈金鑫谢国伟
Owner HONG KONG BAPTIST UNIV
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