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Hole transport material, preparation method thereof, and organic electroluminescent device

一种空穴传输材料、有机的技术，应用在电固体器件、有机化学、电气元件等方向，能够解决空穴传输材料迁移速率不高、HOMO能级和LUMO能级不匹配、影响OLED器件发光效率等问题，达到迁移速率高、高发光效率的效果

Active Publication Date: 2019-11-29
WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides a hole transport material and its preparation method, and an organic electroluminescent device, to solve the problem of the mismatch between the HOMO energy level and the LUMO energy level of the hole transport material and the The technical problem that the mobility rate is not high, which affects the luminous efficiency of OLED devices

Method used

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  • Hole transport material, preparation method thereof, and organic electroluminescent device
  • Hole transport material, preparation method thereof, and organic electroluminescent device
  • Hole transport material, preparation method thereof, and organic electroluminescent device

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preparation example Construction

[0049] Such as figure 1 As shown, this embodiment provides a preparation method of the above-mentioned hole transport material, comprising the following steps:

[0050] S10, mixing the first reactant, the second reactant, palladium acetate and tri-tert-butylphosphine tetrafluoroborate to obtain a mixed solution;

[0051] S20, placing the mixed solution in a glove box, adding sodium tert-butoxide and toluene to the mixed solution, reacting and cooling to room temperature to obtain a reaction solution;

[0052] S30, extracting the reaction solution, merging the organic phases, and separating and purifying the organic phases to obtain the hole transport material.

[0053] Shown in the general structural formula (B) of described first reactant: The structural formula of the second reactant corresponds to the R group, and can be any one of carbazole and its derivatives, diphenylamine and its derivatives, phenoxazine and its derivatives, and acridine and its derivatives kind.

...

Embodiment 1

[0056]Add the first reactant (3.02g, 5mmol), carbazole (1.00g, 6mmol), palladium acetate (45mg, 0.2mmol), tri-tert-butylphosphine tetrafluoroborate (0.17g, 0.6mmol), to obtain a mixed solution, then place the mixed solution in a glove box, then add sodium tert-butoxide (NaOt-Bu, 0.58g, 6mmol) to the mixed solution, and inject 100mL of Toluene, which had been dehydrated and deoxygenated in advance, was reacted at 120°C for 24 hours, and cooled to room temperature to obtain a reaction solution. The reaction solution was poured into 200 mL of ice water, extracted three times with dichloromethane, and the organic phase was combined, and spun into silica gel. Separation and purification by column chromatography (the volume ratio of dichloromethane to n-hexane was 1:5) gave target compound 1, which was 2.2 g of white powder with a yield of 64%. This white powder is carried out mass spectrum analysis and obtains MS (EI) m / z: [M] + : 691.39, the theoretical relative molecular mass of...

Embodiment 2

[0076] Add the first reactant (3.02g, 5mmol) in the 250mL two-necked flask, phenoxazine (1.10g, 6mmol), palladium acetate (45mg, 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17g , 0.6mmol), and then NaOt-Bu (0.58g, 6mmol) was added into the glove box, and 100mL of toluene, which had been dehydrated and deoxygenated beforehand, was injected under an argon atmosphere, and reacted at 120°C for 24 hours. Cool to room temperature, pour the reaction solution into 200mL ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and separate and purify by column chromatography (dichloromethane:n-hexane, v:v, 1:5) to obtain Target compound 2, the target compound 2 is 2.6 g of white powder, and the yield is 74%. MS(EI)m / z:[M] + : 707.32, the theoretical relative molecular mass of the target compound 2 is 707.37.

[0077] Wherein, the synthesis route of the hole transport material is shown in the following formula (2):

[0078] ...

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Abstract

The invention relates to a hole transport material, a preparation method thereof and an organic electroluminescent device. The structural general formula of the hole transport material is as follows,and R group is any one of carbazole groups and derivative groups thereof, diphenylamine groups and derivative groups thereof, phenoxazine groups and derivative groups thereof, and acridine groups andderivative groups thereof. The hole transport material with appropriate energy level and high migration rate is designed and synthesized by taking a diboacridine structure as a core and matching different functional groups, and the organic electroluminescent device based on the hole transport material has higher luminous efficiency.

Description

technical field [0001] The invention relates to the field of display technology, in particular to a hole transport material, a preparation method thereof, and an organic electroluminescent device. Background technique [0002] Organic Light-emitting Diode (OLED) has the advantages of active light emission, high luminous efficiency, large viewing angle, fast response speed, low driving voltage, low energy consumption, lighter and thinner, and its huge application The prospect has received widespread attention from the industry. In OLED light-emitting materials, light-emitting guest materials are crucial to their performance. [0003] The light-emitting guest material used in early OLEDs is fluorescent materials. Since the ratio of singlet and triplet excitons in OLEDs is 1:3, the theoretical internal quantum efficiency (IQE) of OLEDs based on fluorescent materials can only reach 25%. , which greatly limits its application in fluorescent electroluminescent devices; due to th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/16C07F7/08H01L51/50H01L51/54
CPCC07D471/16C07F7/0816C07F7/083H10K85/657H10K85/6572H10K85/40H10K50/15H10K85/631C07C209/74
Inventor 罗佳佳
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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