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Hole transport material and organic electroluminescent device using same

A technology of hole transport materials and hole transport layers, which is applied in the fields of electric solid-state devices, electrical components, organic chemistry, etc., can solve the problem that the thermal stability of hole transport materials is lower than that of light-emitting layer materials or electron transport materials, and achieve Excellent carrier transport ability and stability, increased delocalization, and improved hole transfer rate

Pending Publication Date: 2021-01-22
NANJING TOPTO MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, organic hole transport materials mainly include poly-p-phenylene vinylene (PPv), polythiophenes, polysilanes, triphenylmethanes, triarylamines, hydrazones, pyrazolines, azoles, and carbazoles. class, butadiene, etc., but usually the thermal stability of hole transport materials is still lower than that of light-emitting layer materials or electron transport materials, which has become an important factor affecting the performance of organic electroluminescent devices.

Method used

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  • Hole transport material and organic electroluminescent device using same
  • Hole transport material and organic electroluminescent device using same
  • Hole transport material and organic electroluminescent device using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] 1 is synthesized as follows:

[0042] (1)

[0043]

[0044] Compound 1 (405g / mol, 10g, 24.7mmol), FeCl 3 (0.2eq, 162.2g / mol, 4.94mmol, 0.8g), CS 2 (200g, 20 times the mass of compound 1) was added to the reaction flask, chlorobutane (2.1eq, 92.57g / mol, 51.87mmol, 4.8g) was added under ice cooling, and after the addition was completed, it was slowly returned to room temperature and reacted for 10h. , the reaction solution is poured into ice cubes (400g, the mass of ice cubes is CS 2 2 times the mass of ), hydrochloric acid was added dropwise until the pH of the system reached 2-3, and then dichloromethane (400g, CS 2 2 times the mass of the compound) for extraction, separated the dichloromethane phase and washed it several times with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product of compound 2, which was purified by column chromatography to obtain the pure product of compound 2 (8.77g, har...

Embodiment 2

[0055]

[0056] 2 is synthesized as follows:

[0057] Step 1-2 is basically the same as embodiment 1, and all the other steps are as follows:

[0058] (3)

[0059]

[0060] Under nitrogen protection, compound 4 (12g, 281g / mol, 42.7mmol), compound 7 (1eq, 321.15g / mol, 42.7mmol, 13.71g), sodium tert-butoxide (1.1eq, 96.1g / mol, 46.97mmol , 4.51g), Pd2(dba)3 (5%eq, 915.72g / mol, 2.14mmol, 1.96g), tri-tert-butylphosphine (5%eq, 202.317g / mol, 2.14mmol, 0.43g), toluene (120g, 10 times the mass of compound 4) was added to the reaction flask, and after the addition was completed, the temperature was raised to reflux for 12 hours. After the HPLC detection reaction was completed, after cooling down to room temperature, water was added and stirred for 15 minutes to obtain the filtrate, and the organic phase was obtained after the filtrate was separated. , the organic phase was dried with anhydrous magnesium sulfate and passed through a silica gel funnel to obtain a secondary filtra...

Embodiment 3

[0065]

[0066] 3 is synthesized as follows:

[0067] Step 1-2 is basically the same as embodiment 1, and all the other steps are as follows:

[0068] (3)

[0069]

[0070] Under nitrogen protection, compound 4 (12g, 281g / mol, 42.7mmol), compound 9 (1eq, 378.22g / mol, 42.7mmol, 16.15g), sodium tert-butoxide (1.1eq, 96.1g / mol, 46.97mmol , 4.51g), Pd2(dba)3 (5%eq, 915.72g / mol, 2.14mmol, 1.96g), tri-tert-butylphosphine (5%eq, 202.317g / mol, 2.14mmol, 0.43g), toluene (120g, 10 times the mass of compound 4) was added to the reaction flask, and after the addition was completed, the temperature was raised to reflux for 12 hours. After the HPLC detection reaction was completed, after cooling down to room temperature, water was added and stirred for 15 minutes to obtain the filtrate, and the organic phase was obtained after the filtrate was separated. , the organic phase was dried with anhydrous magnesium sulfate and passed through a silica gel funnel to obtain a secondary filtra...

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PUM

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Abstract

The invention discloses a hole transport material and an organic light-emitting device using the same, wherein the structural formula of the hole transport material is as shown in formula I. The holetransport material contains an arylamine structure, wherein the electron gain and loss mainly occur on nitrogen atoms, and by connecting with a main core, an electron conjugated system around the nitrogen atoms can be increased, the conjugation effect is enhanced, and the quantum efficiency of photoluminescence is greatly improved, so that the transmission of carriers is facilitated; and the delocalization of electrons is increased due to the increase of a conjugation system, so that traps can be reduced in the transmission of the carriers, the carriers are easier to transmit in the conjugation system, the material has good chemical stability, thermal stability and morphological stability, and can effectively improve the aging resistance of the device, prolong the service life and improvethe luminous efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a hole transport material and an organic electroluminescent device using the material. Background technique [0002] Organic light-emitting devices (Organic Light-emitting Devices, OLED) are spontaneous light-emitting devices using the following principle: when an electric field is applied, fluorescent substances emit light through the recombination of holes injected from the positive electrode and electrons injected from the negative electrode. This self-luminous device has the characteristics of low voltage, high brightness, wide viewing angle, fast response, good temperature adaptability, etc., and is ultra-thin, and can be fabricated on flexible panels. It is widely used in mobile phones, tablet computers, TVs, lighting, etc. and other fields. [0003] Organic electroluminescent devices are like a sandwich structure, including electro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C211/55C07D307/91C07D209/88C07D239/26C07D251/24C07D213/74H01L51/50H01L51/54
CPCC07C211/61C07C211/55C07D307/91C07D209/88C07D239/26C07D251/24C07D213/74C07B2200/05H10K85/624H10K85/626H10K85/615H10K85/654H10K85/6574H10K85/6572H10K50/15H10K50/16
Inventor 钱超许军
Owner NANJING TOPTO MATERIALS CO LTD
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