Space charge transfer dendritic fluorescent material, preparation method thereof and organic light-emitting device

A dendritic and fluorescent technology, applied in the direction of luminescent materials, chemical instruments and methods, etc., can solve the problem of low device efficiency

Active Publication Date: 2019-05-10
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the problem with this type of material is that it is difficult to realize the utilization of triplet excitons by thermally activating the delayed fluorescence effect, resulting in low device efficiency.

Method used

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  • Space charge transfer dendritic fluorescent material, preparation method thereof and organic light-emitting device
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  • Space charge transfer dendritic fluorescent material, preparation method thereof and organic light-emitting device

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preparation example Construction

[0116] The present invention also provides a method for preparing a dendritic fluorescent polymer compound as described in any one of the above technical solutions, comprising the following steps:

[0117] 1) Under a protective atmosphere, the iodo compound X-1 is subjected to a Sonogashira coupling reaction with p-bromophenylacetylene to obtain an intermediate X-2;

[0118] 2) Under a protective atmosphere, the intermediate X-2 obtained in the above steps is subjected to a cyclotrimerization reaction to obtain intermediate X-3 and intermediate X-4 respectively;

[0119] 3) Under a protective atmosphere, after performing the first Buchwald–Hartwig reaction on the intermediate X-3 obtained in the above steps and the arylamine compound X-5, a dendritic fluorescent polymer compound with a specific structure of formula (I) is obtained;

[0120] Under a protective atmosphere, the intermediate X-4 obtained in the above steps and the arylamine compound X-5 are subjected to the second...

Embodiment 1

[0167] The chemical structure and synthetic route of I-1 are as follows:

[0168]

[0169] (1), the preparation of intermediate 3: add 1 (8.71g, 20mmol), 2 (4.35g, 24mmol), tetrakistriphenylphosphine palladium (1.16g, 1mmol) in the there-necked flask of 500 milliliters, iodide Copper (0.38g, 2mmol) and triphenylphosphine (0.53g, 2mmol) were replaced with argon and injected with 100ml of anhydrous and oxygen-free tetrahydrofuran and 100ml of triethylamine, respectively, and reacted at 60°C for 24 hours. Cool down to room temperature, add dilute hydrochloric acid and dichloromethane 100mL for extraction, wash twice with dilute hydrochloric acid solution, and wash several times with deionized water. The organic phase was separated, and 5.3 g of the compound with the structure shown in Intermediate 3 was obtained through column separation and desolvation, with a yield of 54%.

[0170] (2), the preparation of intermediate 4 and intermediate 5:

[0171] Under argon atmosphere, ...

Embodiment 2

[0175] The synthetic route is as follows:

[0176]

[0177] Under argon atmosphere, intermediate 5 (0.44g, 0.3mmol), 6 (0.51g, 1.8mmol), Pd 2 (dba) 3 (83mg, 0.09mmol), t-Bu 3 PHBF 4 (105mg, 0.36mmol), t-BuONa (0.35g, 3.6mmol), then inject 20mL of toluene, and react at 110°C for 24 hours. Cool down to room temperature, add deionized water and 100 mL of dichloromethane for extraction, and wash with deionized water several times. The organic phase was separated, and the fluorescent material II-10.29 g was obtained by column separation and solvent removal, with a yield of 47%. C147H126N12 elemental analysis (%): C, 85.68; H, 6.16; N, 8.16; MALDI-TOF (m / z): 2059

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Abstract

The invention provides a dendritic fluorescent high-molecular compound. A structure of the dendritic fluorescent high-molecular compound is as shown in a formula (I) or (II). A dendritic fluorescent material with space charge transfer effects is designed, hexaphenylbenzene with volume restriction effects serves as a core, three dendritic electron donor units and three electron acceptor units are introduced in the periphery, and a space charge transfer dendritic fluorescent material is acquired. The electron donors and electron acceptors are separated on the space, so that low singlet state-triplet state energy level difference is achieved, remarkable thermal activation delayed fluorescence effects are shown, triplet state excitons can be effectively utilized when the material uses as a luminescent material of a solution processing organic light-emitting device, and high luminescent efficiency of the device is achieved, so that the material solves the technical problem that a past device based on chemical bond charge transfer dendritic fluorescent material is low in efficiency.

Description

technical field [0001] The invention relates to the field of organic light-emitting materials, to a dendritic fluorescent polymer compound and a preparation method thereof, and an organic electroluminescent device, in particular to a dendritic fluorescent material with space charge transfer effect and a preparation method thereof, and an organic electroluminescence light-emitting device. Background technique [0002] Organic light-emitting devices (OLEDs) are usually composed of a cathode, an anode, and an organic layer interposed between the cathode and the anode, that is, the device is composed of a transparent ITO anode, a hole injection layer (TIL), and a hole transport layer (HTL). , the light emitting layer (EL), the hole blocking layer (HBL), the electron transport layer (ETL), the electron injection layer (EIL) and the cathode are formed, and 1-2 organic layers can be omitted as needed. The mechanism of action is that a voltage is formed between the two electrodes, ...

Claims

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Application Information

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IPC IPC(8): C08G83/00C09K11/06
Inventor 王利祥王兴东邵世洋王淑萌吕剑虹
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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