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Efficient red light electroluminescence material processed by solution using naphthothiadiazole as luminous center

An electroluminescent material, a technology of naphthothiadiazole, applied in the direction of luminescent materials, circuits, electrical components, etc.

Inactive Publication Date: 2009-12-02
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The current progress in solution-processed small molecule compounds and devices is encouraging, but the efficiency still needs to be further improved, and the research on new compound systems is still an important topic in this field

Method used

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  • Efficient red light electroluminescence material processed by solution using naphthothiadiazole as luminous center
  • Efficient red light electroluminescence material processed by solution using naphthothiadiazole as luminous center
  • Efficient red light electroluminescence material processed by solution using naphthothiadiazole as luminous center

Examples

Experimental program
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Effect test

Embodiment 1

[0076] Example 1: Synthesis of red photoluminescent materials with electroactive units

[0077] We only take the synthesis of the compound with the following structure as an example to illustrate the present invention, rather than to limit the present invention. All the synthesis idea or synthesis route of red photoluminescent material, and its preparation into luminescent thin film by solution processing method are all within the scope of the design idea of ​​the present invention.

[0078] synthetic route

[0079]

[0080] 1. Synthesis of 4,7-dichloro-2,1,3-naphthothiadiazole (M1)

[0081] Add 500mg of diaminonaphthalene and 5ml of SOCl into the two-necked bottle 2 , slowly add 0.5ml of pyridine while stirring, raise the temperature to 60°C, reflux for 24 hours, pour the product into water, produce a large amount of precipitate, filter and dissolve in 10ml of DMF, extract three times with water and chloroform, dry, and then evaporate the solvent , to obtain dark orange...

Embodiment 2

[0090] Example 2: Photoluminescent properties of red photoluminescent material TCNzC

[0091] Such as figure 1 The UV-Vis absorption and fluorescence spectra of the red compound TCNzC in dilute tetrahydrofuran solution and spin-coated film are shown. Whether in solution or in film, the UV absorption peaks of TCNzC are at 265nm, 298nm, 332nm, and 505nm, among which the absorption peaks at 265nm and 298nm can be attributed to the characteristic absorption of the carbazole group, and the absorption peak at 332nm can be attributed to The characteristic absorption of the fluorene group, the broad absorption at 505nm is attributed to the characteristic absorption of the 2,1,3-naphthothiadiazole group. In solution, under the excitation of 320nm light, the emission peak of TCNzC is located at 599nm, which is the emission generated by the efficient transfer of the energy of carbazole and fluorene excitons to the naphthothiadiazole unit, which shows that naphthothiadiazole As an excit...

Embodiment 3

[0092] Example 3: Device properties of TCNzC solution processed spin-coated films

[0093] Since TCNzC has a relatively large molecular structure and a relatively large molecular weight (Mw=1512.0), it can be processed by solution spin coating like a polymer, making the preparation of the device more convenient and more conducive to future practical applications. So we dissolved TCNzC in chloroform (20 mg / ml) and spin-coated it on the ITO substrate at 3000 rpm. From image 3 It can be seen that the surface morphology of TCNzC films prepared by spin coating is very smooth, and the square root roughness is only 0.32nm. Such a smooth surface morphology is necessary for organic electroluminescent devices, so we can prepare TCNzC light-emitting thin films by spin coating.

[0094] Since TCNzC can form a uniform and flat film by spin coating, we used a preparation method similar to polymer devices to prepare a device structure of ITO / PEDPT / TCNzC (spin coating film) / TPBi (60nm) / LiF...

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Abstract

The invention belongs to the field of organic luminescence, and particularly relates to a red light electroluminescence material using naphthothiadiazole as a luminous center. The red light electroluminescence material can be prepared into a high electroluminescence film used for an organic electroluminescence device by using a solution processing method or an electrochemical polymerization method. The luminous center connected with an electroactive unit consists of an efficient naphthothiadiazole red light unit and efficient dark-blue light emitting units at two sides. The dark-blue light emitting units are fluorene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene and derivatives formed by mutually bonding the substances. The electroactive unit is carbazole, thiofuran, pyrrole, ethylene, ethyne, phenylamine, diphenylamine or triphenylamine. A connecting chain of the electroactive unit and the light emitting unit is an alkyl chain, an oxygen chain or an alkoxyl chain, and the electroactive unit and the light emitting unit also can be directly connected. The luminous efficiency of a device using the red light material reaches 5.8cd / A, and has high level in the red light devices prepared by electrochemical deposition.

Description

technical field [0001] The invention belongs to the field of organic luminescence, and specifically relates to a red photoluminescent material with electroactive groups, which uses naphthothiadiazole as a luminescent center. The red photoluminescent material can be processed by a solution, Electroluminescent thin films with high luminous efficiency can also be prepared by means of electrochemical polymerization, and then applied to organic electroluminescent devices. Background technique [0002] Organic / polymer electroluminescent devices have been developed by leaps and bounds in the past ten years. Since 2000, OLED, a new flat-panel display technology, has received great attention from the industry and has begun to enter the stage of industrialization. [0003] The compounds used to fabricate OLED devices are mainly divided into two categories: small molecules based on vacuum evaporation and conjugated polymers based on solution processing. Vacuum evaporation technology ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D417/14H01L51/50H01L51/54H01L51/56
Inventor 马於光顾成陆丹张明费腾王奇吕营
Owner JILIN UNIV
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