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Novel OLED (organic light emitting diode) material and application thereof

A new type of luminescent material technology, applied in the field of small molecule OLED materials and organic electroluminescence, can solve the problems affecting the development of organic electroluminescence devices, and achieve the effect of good efficiency and good film stability

Active Publication Date: 2013-08-28
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, red light-emitting materials and green light-emitting materials are relatively mature, but efficient and stable blue light-emitting materials, especially deep blue light-emitting materials, are still scarce, which largely affects the development of organic electroluminescent devices.

Method used

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  • Novel OLED (organic light emitting diode) material and application thereof
  • Novel OLED (organic light emitting diode) material and application thereof
  • Novel OLED (organic light emitting diode) material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Preparation and structural characterization of intermediates 3-(3,5-dibromophenyl)pyridine 1 and 3-(3-bromo-5-(3-pyridine)-phenyl)pyridine 2:

[0057] Synthesis of intermediates 1 and 2:

[0058] In a 500mL three-necked flask, add s-tribromobenzene (12.6g, 40mmol), pyridine-3-boronic acid (10.5g, 85mmol), K 2 CO 3 (22g, 160mmol), dioxane (160mL), deionized water (80mL), N 2 protection, adding Pd(PPh 3 ) 4 (800mg), reflux reaction for 18 hours, TLC analysis, the ratio of monosubstituted product 1 to double substituted product 2 is about 2:1, stop the reaction. Separation, collecting the organic phase, anhydrous Na 2 SO 4 Dry, filter, and remove the solvent. The crude product is subjected to silica gel column chromatography and gradient elution. First, petroleum ether is used, and then petroleum ether: ethyl acetate = 1:2 to collect the monosubstituted product 1 and the disubstituted product 2, respectively. 15.0 g of the monosubstituted product was obtained with a...

Embodiment 2

[0064] Preparation and properties of Example 2 OLED material 4PySF:

[0065] 1. Synthesis and structural characterization of OLED material 4PySF:

[0066] In a 250mL three-necked flask, add 2,7-spirobifluorene borate (1.7g, 3mmol), intermediate 2 (2.05g, 6.6mmol), K 2 CO 3 (4.1g, 30mmol), N,N-dimethylacetamide (60mL), deionized water (25mL), Pd(PPh 3 ) 4 (500mg), N 2 Protection, reflux reaction for 24 hours, stop reaction. Add 50 mL of water, stir for 10 min, filter with suction, rinse the filter cake with 50 mL of methanol, collect the filter cake, and purify the filter cake by silica gel column chromatography, the eluent is methanol:ethyl acetate=1:10, and 0.82 g of the target product is obtained. The yield was 35.2%. The chemical vapor deposition system was used for further sublimation and purification. The sublimation temperature was 345°C, and 0.38g of the target product was obtained, with a yield of 16.3%.

[0067] 1 H NMR (CDCl 3 ,TMS,500MHz):8.852-8.856(d,4H,J=...

Embodiment 3

[0071] Example 3 Application of OLED material 4PySF in organic electroluminescent devices

[0072] This embodiment prepares dark blue organic electroluminescent device according to the following method:

[0073] a) Clean ITO (indium tin oxide) glass: ultrasonically clean the ITO glass with deionized water, acetone, and ethanol for 30 minutes each, and then treat it in a plasma cleaner for 5 minutes;

[0074] b) Vacuum-evaporated hole transport layer NPB on the anode ITO glass with a thickness of 50nm;

[0075] c) On top of the hole transport layer NPB, 4PySF, which serves as both the light-emitting layer and the electron transport layer, is vacuum-evaporated with a thickness of 60 nm;

[0076] d) On top of 4PySF, vacuum evaporated electron injection layer LiF with a thickness of 1nm;

[0077] e) On top of the electron injection layer LiF, a cathode Al is vacuum-evaporated with a thickness of 100 nm.

[0078] The structure of the device is ITO / NPB(50nm) / 4PySF(60nm) / LiF(1nm) / ...

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Abstract

The invention relates to a novel OLED (organic light emitting diode) material and an application thereof. By taking 9,9'-spirobifluorene as the center and introducing a substituent group (3,5-dipyridylbenzene) with electronic transmission performance to a live position of 9,9'-spirobifluorene, a novel OLED material which can be used as a deep blue electroluminescent material as well as an electronic transmission material is obtained. The novel OLED material provided by the invention has good film stability and proper molecular energy level, and can be used as a luminous material and / or electronic transmission material in the field of organic electroluminescence.

Description

technical field [0001] The present invention relates to a novel OLED material and its application, in particular to a small molecule OLED material containing 9,9'-spirobifluorene and 3,5-dipyridylbenzene structural units, and to the application of the material in organic electrophoresis Applications in the field of luminescence. Background technique [0002] Compared with traditional liquid crystals, organic light-emitting diodes (hereinafter referred to as OLEDs) have many advantages such as self-illumination, wide viewing angle, fast response speed, and flexible display, which make them the most favorable competitors for next-generation display technology. People pay great attention. After more than 20 years of continuous development, nowadays, a variety of products based on OLED display technology have been industrialized. Nevertheless, organic electroluminescent devices still have many problems such as short lifespan and low efficiency, which need to be further explore...

Claims

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Application Information

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IPC IPC(8): C09K11/06H01L51/54
Inventor 盛磊王元勋肖立新陈志坚龚旗煌郝明
Owner VALIANT CO LTD
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