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A kind of bis-triarylamine substituted phosphineoxytriphenylene compound, intermediate, preparation method and application

A phosphineoxybenzene and compound technology, applied in the field of organic electroluminescence, can solve the problems of poor performance, affecting the efficiency and life of the device, limiting performance, etc., to achieve balanced electron and hole transport capabilities, thermal stability performance guarantee, balance The effect of transmission

Active Publication Date: 2016-04-20
KUNSHAN VISIONOX DISPLAY TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as one of the three materials for white light devices, the performance of blue phosphorescent materials is still inferior to that of red phosphorescent materials and green phosphorescent materials. The instability caused by energy, the second is that it is difficult to find suitable host materials with high triplet energy levels and suitable LUMO, HOMO energy levels, and high and balanced carrier transport capabilities, so the current blue light materials are still Fluorescent dyes are mainly used
But CBP still has obvious defects: the glass transition temperature T g Very low, only 62°C, and CBP is used as a hole-type transport material, and its corresponding electron transport ability is not balanced enough, which affects the efficiency and life of the device
In general, bipolar materials are designed by combining electron-rich (electron donor) and electron-deficient (electron acceptor) functional groups. Between the donor and the acceptor, the energy gap becomes smaller and the energy of the triplet state decreases, which limits the performance of this type of compound as a blue phosphorescent host, but it can be used as a host material for green and red phosphorescent materials.

Method used

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  • A kind of bis-triarylamine substituted phosphineoxytriphenylene compound, intermediate, preparation method and application
  • A kind of bis-triarylamine substituted phosphineoxytriphenylene compound, intermediate, preparation method and application
  • A kind of bis-triarylamine substituted phosphineoxytriphenylene compound, intermediate, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] The structural formula and synthetic route of the intermediate S1 to be prepared in this example are as follows:

[0078]

[0079]

[0080] Specific steps:

[0081] (1) 1-bromo-3-chloro-7-methylnaphthalene (59 grams, 231mmol) was dissolved in 500mL carbon tetrachloride, heated to reflux, NBS (34.7g, 194mmol) and benzoyl peroxide (0.59g, 2.45mmol) was added into the above solution in three equal parts, wherein, NBS and benzoyl peroxide were added together and added once every 1 hour, and the resulting mixture was stirred at 75°C for 40 hours, cooled to room temperature, and filtered , concentrated the filtrate, and the residue was recrystallized (petroleum ether) to obtain 59 g of white solid 1-bromo-3-chloro-7-bromomethylnaphthalene, MS (m / z) MS (m / z): 334, yield 76%.

[0082] (2) Dissolve the obtained 1-bromo-3-chloro-7-bromomethylnaphthalene (44 g, 132 mmol) in 250 mL of toluene, then add triphenylphosphine PPh 3 (34.6g, 132mmol), heated to reflux for 4 hours...

Embodiment 2

[0088] The intermediate S2 required to be prepared in this embodiment has a structural formula and a synthetic route as follows:

[0089]

[0090]

[0091] The specific steps are: under the protection of nitrogen, a catalytic amount of iodine and activated magnesium chips (8.4g, 350mmol) are added to 300mL tetrahydrofuran, and then 3,10-dichloro-1,12-dibromobenzo[ c] phenanthrene (31.9g, 70mmol) tetrahydrofuran solution 700mL, (add 30ml first, and then drop the remaining solution after triggering), after the dropwise addition, the resulting mixture continues to reflux for 6 hours, cool, and the resulting solution is filtered to another In the dry reaction flask, the temperature was lowered to 0°C, and a tetrahydrofuran solution (50 mL) of 4-fluorophenylphosphine dichloride (13.8 g, 70 mmol) was added dropwise (see J.Chem.Soc., DaltonTrans., 2007, 272)), after adding, naturally rise to room temperature, continue to react for 4 hours and dilute with diethyl ether, quench w...

Embodiment 3

[0095] The intermediate S3 required to be prepared in this embodiment has a structural formula and a synthetic route as follows:

[0096]

[0097] The chemical equation of the whole reaction process is:

[0098]

[0099] The specific steps are: under the protection of nitrogen, a catalytic amount of iodine and activated magnesium chips (8.4g, 350mmol) are added to 300mL tetrahydrofuran, and then 3,10-dichloro-1,12-dibromobenzo[ c] phenanthrene (31.9g, 70mmol) tetrahydrofuran solution 700mL, (add 30ml first, and then drop the remaining solution after triggering), after the dropwise addition, the resulting mixture continues to reflux for 6 hours, cool, and the resulting solution is filtered to another In the dry reaction flask, cool down to 0°C, add 2-pyridylphosphine dichloride (12.6g, 70mmol) in tetrahydrofuran solution (50mL) dropwise (see J.Chem.Soc., DaltonTrans., 2007, 272 )), after adding, naturally rise to room temperature, dilute with diethyl ether after continui...

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Abstract

The invention relates to a bipolar organic material having phosphonooxy functional group and triaromatic amine functional group. The compounds have the general formula (Pn), wherein Ar1, Ar2, Ar3, Ar4 and Ar5 are, independently from one another, aryl or heteroaryl, R1 to R4 are, independently from one another, H, alkanyl, alkoxy hydrocarbyl, naphthenic alkyl, aryl or heteroaryl. The bipolar compounds provided by the invention are used as a body material of triplet luminescent dyes or a carrier transport material, have the characteristics of high carrier transport capacity and high stability. Besides, the compounds can transport both electrons and holes, effectively ensure the charge transport balance of a luminescent layer to increase the brightness and efficiency of a corresponding organic electroluminescent device and prolong the service life of the organic electroluminescent devices, and overcome the deficiencies of low efficiency and short service life of organic electroluminescent devices under heavy-current conditions.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and specifically relates to a bipolar organic material designed based on phosphorus-oxygen functional groups and triarylamine and a preparation method thereof, as well as its main material for phosphorescence emitting layers in organic electroluminescence devices, electronic or application in hole transport materials. Background technique [0002] Organic Light Emitting Diode (OLED) is a current-driven light-emitting device that uses organic materials as active materials, specifically refers to organic semiconductor materials and organic light-emitting materials that are driven by an electric field to cause light emission through carrier injection and recombination Technology. Unlike inorganic materials, organic materials have the characteristics of low synthesis cost, adjustable function, flexibility, and good film-forming properties. Moreover, devices based on organic materials are ...

Claims

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Application Information

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IPC IPC(8): C07F9/6568H01L51/54
Inventor 邱勇范洪涛李建仁李银奎
Owner KUNSHAN VISIONOX DISPLAY TECH
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