Substituted benzophenanthrene derivative organic light emitting diode material

A light-emitting diode and organic technology, applied in the field of organic light-emitting diode materials that replace triphenylene derivatives, can solve problems such as degradation, high crystallinity, and poor thermal stability, and achieve the effects of improved efficiency and high thermal stability

Inactive Publication Date: 2015-04-29
GUANMAT OPTOELECTRONICS MATERIALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Although these materials offer some good luminescent properties, they all have some disadvantages: (1) they have low glass transition temperature and poor thermal stability, and they may degrade during high-temperature deposition in vacuum; (2) high crystallinity
But the disadvantage is that coplanar triphenylene often brings solubility and too strong intermolecular force, which makes the device performance poor.

Method used

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  • Substituted benzophenanthrene derivative organic light emitting diode material
  • Substituted benzophenanthrene derivative organic light emitting diode material
  • Substituted benzophenanthrene derivative organic light emitting diode material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0123] Example 1. Synthesis of Compound 42 (M5)

[0124] .

[0125] （ 1 ) Intermediate M1 Synthesis

[0126] In a 250 mL three-necked flask with a thermometer and a condenser, add 72 g (250 mmol) of 3-bromophenanthrenequinone, 58 g (276 mmol) of dibenzyl ketone, 7 g (125 mmol) of KOH, and 800 ml of ethanol, and heat to reflux. Reaction for 1h. The TLC dot plate monitors the reaction to completion. Cool to room temperature, filter, wash the filter residue with methanol, and filter to obtain the desired product. 58g (42%) of brown solid is received; it is directly used in the next reaction without purification.

[0127] （ 2 ) Intermediate M2 Synthesis

[0128] In a 1000 mL three-necked flask with a thermometer and a condenser, 58 g (125.5 mmol) of M1, 24.6 g (200 mmol) of trimethylsilyl acetylene, and 350 ml of o-xylene were sequentially added, and the temperature was raised to reflux for 12 hours. Cooled to room temperature, filtered, the filtrate was reversed-phase precipitati...

Embodiment 2

[0135] Example 2. Synthesis of compound 10

[0136] .

[0137] （ 1 ) Intermediate 3- Boron ester -5,8- Synthesis of diphenyltriphenylene

[0138] In a 100 mL three-necked flask with a thermometer and a condenser, add 0.92g (2mmol) of 3-bromo-5,8-diphenyltriphenylene, Pinacol diborate 0.61g (2.4 mmol), tribenzylidene acetone dipalladium 0.04g (0.04 mmol), S-phos 0.03g (0.08mmol), potassium acetate 0.4g (4 mmol), toluene 20ml, replaced with nitrogen, heated to reflux for reaction 16h. Cool to room temperature, filter, collect the filtrate, use a short silica gel column, use pure n-hexane as mobile phase: dichloromethane=4:1, and receive 0.68g (68%) of white solid, MS=612.

[0139] （ 2 ) Synthesis of the final product

[0140] In a 100 mL three-necked flask with a thermometer and a condenser, add 0.6 g (1.2 mmol) of 3-boron ester-5,8-diphenyltriphenylene, 9- bromine -10-(2- Naphthyl ) Anthracene 0.383g (1 mmol), Pd(PPh 3 ) 4 0.02g (0.016 mmol), potassium carbonate 0.175g (1...

Embodiment 3

[0141] Example 3. Synthesis of compound 52 (M7)

[0142] .

[0143] （ 1 ) Intermediate M6 Synthesis

[0144] In a 100 mL three-necked flask with a thermometer and a condenser, 22.8g (109mmol) of 2-amino-9,9-dimethylfluorene, 19.2g (72.87mmol) of 2-bromodibenzofuran, Sanya 1 g (1.09 mmol) of dipalladium benzylacetone, 1.35 g (21.8 mmol) of BINAP, 13.9 g (145 mmol) of sodium tert-butoxide, 180 ml of toluene, replaced with nitrogen, heated to reflux and reacted for 3h. Cool to room temperature, filter, collect the filtrate, use a short silica gel column, use pure n-hexane: dichloromethane = 4:1 as the mobile phase, and receive 23.2 g (85%) of white solid.

[0145] （ 2 ) Synthesis of the final product

[0146] In a 100 mL three-necked flask with a thermometer and a condenser, add 0.45 g (1.2 mmol) of M6, 0.458 g (1 mmol) of M3, 0.048 g (0.05 mmol) of tribenzylidene acetone, and P(t- Bu) 3 0.16g (0.2mmol), 0.38g (4mmol) of sodium tert-butoxide, 25ml of toluene, replaced with nitrog...

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Abstract

The invention discloses a substituted benzophenanthrene derivative organic semiconductor (I). By taking a benzophenanthrene derivative as a main core, the main core is chemically bonded and connected with a cavity or condensed with a heteroaromatic ring through teleportation. The material has the light emitting characteristics of excellent heat resistance and efficient long service life and can be applied to a blue light main body material, a blue light emitting layer, a cavity transmission layer or an electronic barrier layer of an organic light emitting diode to obtain an organic light emitting apparatus which is stable, efficient and long in service life.

Description

technical field [0001] The invention relates to an organic light-emitting material and its application in an organic light-emitting device, in particular to an organic semiconductor material with both high efficiency and long life, which can be applied to an organic light-emitting OLED device to improve device performance. Background technique [0002] Organic semiconductor materials are new types of optoelectronic materials. Its large-scale research originated in 1977 when Hideki Shirakawa, A. Heeger and A. McDiamid jointly discovered doped polyacetylene with a conductivity up to copper level. Subsequently, in 1987, C. Tang of KodaK Company invented the organic small molecule light-emitting diode (OLED), and in 1990, R. Friend and A. Holmes of Cambridge University invented the polymer light-emitting diode P-OLED, and in 1998, S. Forrest and M. Thomson invented a more efficient organic phosphorescent light-emitting diode PHOLED. Because organic semiconductor materials have ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/62C07D209/82C07D307/91C07D333/76C07C211/61C07F7/10C07C323/38C07C217/78C07C225/22C07F9/53C09K11/06H01L51/54
Inventor 李晓常洪海兵
Owner GUANMAT OPTOELECTRONICS MATERIALS INC
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