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Organic electroluminescent material and organic electroluminescent device

An electroluminescent material and electroluminescent technology, applied in the direction of luminescent materials, electro-solid devices, electrical components, etc., can solve the problems of short lifespan of thermally stable devices and few materials, and achieve improved lifespan, high electron transmission and The effect of injection ability, good thermal stability

Active Publication Date: 2015-02-11
BEIJING AGLAIA TECH DEV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these representative host materials often limit their applications due to their thermal stability and short lifetime of fabricated devices.
[0005] Although after 20 years of development, organic electroluminescent devices have made great progress and development, and organic materials are also continuously developing. Materials with good performance and stability are still rare

Method used

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  • Organic electroluminescent material and organic electroluminescent device
  • Organic electroluminescent material and organic electroluminescent device
  • Organic electroluminescent material and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1: compound ANP8 is synthesized

[0055]

[0056] Synthesis of intermediate 3

[0057] Add acenaphthylquinone (84g, 0.46mol), 1,3-diphenylacetone (72.8g, 0.34mol), 600ml ethanol, and 56g potassium hydroxide into a four-necked flask, start stirring, blow nitrogen gas, and reflux for 2 hours. Cool at room temperature, filter, and rinse the filter cake twice with ethanol to obtain 130 g of a black solid with a yield of 91%.

[0058] Synthesis of compound ANP8

[0059] Intermediate 3 (3.56 g, 10 mmol) and Intermediate 4 (4.69 g, 40 mmol) were mixed under nitrogen and heated to reflux for 48 hours (external temperature 280° C.). The resulting brown solution was cooled to obtain a brown solid, which was crystallized from dichloromethane-acetone after passing through a silica gel column using petroleum ether as the eluent to obtain ANP 8 as white crystals. 0.23 g of product was obtained, yield 5%. ESI-MS m / s calculated value C 34 h 23 N: 445.18, measured va...

Embodiment 2

[0060] Embodiment 2: compound ANP34 is synthesized

[0061]

[0062] Intermediate 3 (3.56g, 10mmol) and Intermediate 6 (7.17g, 40mmol), 60ml of diphenyl ether were mixed under nitrogen and heated to reflux for 48 hours (external temperature 280°C). The resulting brown solution was cooled to obtain a brown solid, which was crystallized from dichloromethane-acetone after passing through a silica gel column using petroleum ether as the eluent to obtain ANP34 as light yellow crystals. 1.37 g of product were obtained, a 27% yield. 1 H NMR (400MHz, CDCl 3 ,δ): 7.98–7.95(m,2H), 7.90–7.82(m,2H), 7.65–7.31(m,20H), 6.93–6.89(d,1H). See Figure 5 . MALDI-TOF-MS m / s calculated value C 39 h 25 N: 507.20, measured value [M+H] + :508.50. See image 3

Embodiment 3

[0063] Embodiment 3: compound ANP64 is synthesized

[0064]

[0065] Intermediate 3 (3.56g, 10mmol) and Intermediate 8 (4.30g, 5mmol, synthesized according to Organic & Biomolecular Chemistry, 10(24), 4704-4711; 2012), 60ml of diphenyl ether were mixed and heated under nitrogen Reflux for 48 hours (external temperature 280°C). The resulting brown solution was allowed to cool to give a brown solid which was crystallized from dichloromethane-acetone to afford ANP64 as white crystals. 2.15 g of product were obtained, yield 50%. 1 H NMR (400MHz, CDCl 3 ,δ): 7.98–7.94 (m, 2H), 7.87–7.77 (m, 2H), 7.67–7.22 (m, 18H), 6.96 (d, 1H, J=10Hz), 1.23 (s, 6H). See Figure 6 . 13 C NMR (100MHz, CDCl 3 ,δ): 27.8, 47.1, 119.6120.3, 122.6, 123.6, 124.9, 125.3, 127.0, 127.3, 127.4, 127.9, 128.0, 128.1, 128.8, 129.0, 129.5, 130.0, 130.5, 130.9, 1343.2. See Figure 7 . ESI-MS m / z calculated value C 42 h 29 N: 547.23, measured value [M+H] + :548.53. See Figure 4 .

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Abstract

The invention relates to an organic electroluminescent material and an organic electroluminescent device. The organic electroluminescent material has a structure represented by a formula (I) shown in specifications. According to the organic electroluminescent device disclosed by the invention, an acenaphtho[1, 2-c]pyridinyl group-containing compound is adopted as an electron transport material, has relatively high electron transport and injection capability and has very good thermal stability and good film forming property, so that the service life of the device is prolonged while the efficiency of the organic electroluminescent device is increased; meanwhile, the organic electroluminescent device disclosed by the invention adopts the acenaphtho[1, 2-c]pyridinyl group-containing compound as a phosphorescent main material, and the acenaphtho[1, 2-c]pyridinyl group-containing compound has a relatively high triplet energy level and has a very good electron transport property, so that the number of electrons in a luminescent layer can be effectively increased, and the efficiency of the device is increased.

Description

technical field [0001] The invention relates to a novel organic electroluminescent material, which is deposited into a thin film by vacuum evaporation and used as an electron transport material or a phosphorescence host material on an organic electroluminescent diode, belonging to the technical field of display of organic electroluminescent devices. Background technique [0002] As a new type of display technology, organic electroluminescent devices have self-illumination, wide viewing angles, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, flexible, bendable and Due to the unique advantages of transparent display panels and environmental friendliness, organic electroluminescent device technology can be applied to flat panel displays and new-generation lighting, and can also be used as a backlight source for LCDs. Since 1987, Tang et al. of Kodak used vacuum film evaporation technolo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D221/18C07D401/14C07D405/14C07D409/14C07D401/04C07D401/10C07D409/04C07D405/04C07D413/10C07F7/10C07D487/04C07F9/576H01L51/54
CPCC07D221/18C09K11/06C07D401/14C07D405/14C07D401/04C07D401/10C07D405/04C07D409/04C07D409/14C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/1074C09K11/02C09K2211/1007C09K2211/1011H10K85/6572H10K85/342H10K50/16H10K50/11H10K2101/10H10K85/615H10K50/121
Inventor 鲁锦鸿戴雷陈金鑫蔡丽菲
Owner BEIJING AGLAIA TECH DEV
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