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Organic electroluminescence ethereal blue optical material, preparation method and application thereof

A coupling reaction and reaction process technology, applied in the field of organic electroluminescence materials, can solve the problems of limited electroluminescence applications and difficult regulation, and achieve high electric field and thermal stability, good amorphousness, and good stability Effect

Inactive Publication Date: 2011-06-15
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the synthesis of spirocyclic trylene derivatives, it is difficult to introduce active and modifiable sites on the backbone with the current methods and target molecule design, which makes it difficult to realize the regulation of the effective conjugation length of the system, making the electroluminescent On the one hand, the use is limited (because the fluorescence of the spirocyclic trisindene itself is not in the visible light region, it needs to be moved to the visible light region by connecting more π-conjugated groups)

Method used

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  • Organic electroluminescence ethereal blue optical material, preparation method and application thereof
  • Organic electroluminescence ethereal blue optical material, preparation method and application thereof
  • Organic electroluminescence ethereal blue optical material, preparation method and application thereof

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Embodiment 1

[0034] Embodiment 1: Preparation of 1a and its property determination

[0035] Use 2-bromo-3', 5-dimethoxybiphenyl to form a lithiated reagent under the action of tert-butyllithium at -78°C and attack the triketone compound. After acidification, a tertiary alcohol is obtained, and then in acetic acid and a catalytic amount Under the condition of methanesulfonic acid, a pale yellow solid was precipitated by ring closure. Suction filter the solid, wash with ethanol, and dry to obtain compound A, and then obtain intermediate 2a by bromination, and carry out Suzuki coupling reaction with spirobifluorene boronate under the catalysis of palladium catalyst to obtain the blue light material of the present invention 1a. The specific reaction process of preparing intermediate 2a is shown in the following formula:

[0036]

[0037] (1) Preparation of compound A:

[0038] Dissolve 2.93 g (10 mmol) of 2-bromo-3', 5-dimethoxybiphenyl in tetrahydrofuran (40 mL), and add a pentane solut...

Embodiment 2

[0045] Embodiment 2: Preparation of 1b and its property determination

[0046] Starting from the industrial raw material m-bromoanisole, through the Friedel-Crafts acetylation of the para-position of the methoxy group, the two-step reaction of the acetyl trimerization promoted by silicon tetrachloride can obtain the tribromo compound in a higher yield; and then in Under the action of -78°C and tert-butyl lithium, the tribromo compound undergoes lithium-halide exchange to obtain a lithiated reagent. At this time, 2,7-dibromofluorenone is added to quench the carbanion, and the tertiary alcohol is obtained after acidification ; Finally, this tertiary alcohol is dissolved in dry dichloromethane, and boron trifluoride ether is added as a Lewis acid in a catalytic amount, and a white solid is precipitated in the system, which is the intermediate product 2b. After adding ethanol to quench the system After boron trifluoride, the solid was suction filtered, washed with ethanol several ...

Embodiment 3

[0059] Embodiment 3: device making

[0060] The typical device manufacturing process of the present invention is as follows: ITO (indium tin oxide) glass is ultrasonicated for ten minutes with acetone, alkaline washing solution, pure water (twice), and isopropanol, and then treated with ozone plasmar for 5 minutes. The hole injection layer PEDOT was spin-coated into a film with a thickness of 60 nm on the treated substrate, and the vacuum oven was kept at 80° C. overnight. Then the hole transport layer PVK (thickness 40nm) and the light emitting layer (1a or 1b50mg / mL toluene solution, thickness 70nm) were sequentially processed by spin coating respectively. The hole blocking layer TPBI (thickness 40nm) is vacuum evaporated on it (1-2A / s, 5×10 -4 pa), and finally Ba / Al (with a thickness of 4nm / 200nm) is vacuum-evaporated on it to form a complete device. The device structure is ITO / PEDOT(60nm) / PVK(40nm) / 1a or1b / TPBI(40nm) / Ba(4nm) / Al(200nm). Among them, the light-emitting lay...

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Abstract

The present invention provides organic small pure blue materials with high stability. The pure blue materials have a structure as shown in formula 1; wherein, R1 stands for Pi-conjugated group; R2 stands for hydrogen, alkyl and alkoxy; and R3 stands for hydrogen, alkyl and alkoxy. The acid-catalyzed Friedel-Crafts ring-closure reaction in the molecules and the high-efficiency palladium-catalyzed coupling reaction solve the problem of molecular synthesis. The compounds have a structure with a spiral ring; the molecules consist of two mutually vertical structural units; thus the larger size andthe branching structure effectively prevent the aggregation of the molecules; and the high-purity blue light can be prepared. The spiral-ring structure with sp<3> hybridized central carbon atoms has relatively high stability; thus the compounds have excellent stability. The compounds can be used as electroluminescent diodes on the light-emitting layer to send pure blue fluorescence, and have high electric and thermal stability.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a new type of stable π-conjugated organic small molecule compounds, which can be used as pure blue light materials in the light-emitting layer of organic electroluminescent diodes (OLEDs). Background technique [0002] In recent years, organic light-emitting diodes (OLEDs) have gradually become an important development direction in the field of flat-panel displays. It is a multi-layer device, which injects holes and electrons by applying an electric field to the anode and cathode at both ends, meets and recombines excitons in the organic light-emitting layer in the middle, and finally releases energy from the excitons to emit visible light. Compared with the traditional liquid crystal display (LCD), OLED has the characteristics of self-luminescence without background light source, simple process and low cost, no viewing angle problem and flexible screen display...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/21C07C43/225C07C41/18H01L51/50H01L51/54
Inventor 裴坚罗佳马玉国
Owner PEKING UNIV
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