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2,7-dibromo-9-hydroxyl phenanthrene derivatives and preparation method thereof

A technology of hydroxyphenanthrene derivatives, which is applied in the field of 2,phenanthrene derivatives and their preparation, can solve problems such as light blue light emission and complex synthesis of bicyclic systems, and achieve improved solubility, easy availability of raw materials, and high yield Effect

Inactive Publication Date: 2012-11-14
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compounds detailed here include 3,6,9,10-tetraphenyl substituted phenanthrenes, and although they are preferred over compounds substituted at the 9,10-position, they still suffer from the disadvantage of 3,6-substitution , so the light emission is light blue
[0005] JP2003 / 055276 describes phenanthrene derivatives for blue-emitting OLEDs. The phenanthrene derivatives contain a bicyclic aliphatic group fused at the 9,10-position, which can also be substituted at the 2,7-position. However, these compounds The disadvantage of fused bicyclic ring systems has to be synthesized in a complicated manner

Method used

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  • 2,7-dibromo-9-hydroxyl phenanthrene derivatives and preparation method thereof
  • 2,7-dibromo-9-hydroxyl phenanthrene derivatives and preparation method thereof
  • 2,7-dibromo-9-hydroxyl phenanthrene derivatives and preparation method thereof

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Effect test

example 1

[0019] Example 1: Synthesis of 2,7-dibromophenanthrenequinone

[0020]

[0021] Under full stirring, 17.95 g NBS was added to 98% concentrated sulfuric acid containing 10 g 9,10-diphenanthrenequinone, and the stirring was continued for 3 h at room temperature, then the mixture was poured on ice cubes, the organic matter was filtered, washed with cold water, and the crude product Recrystallized with DMSO to obtain 13 g orange-red 2,7-dibromophenanthrenequinone, yield: 75%.

[0022] 1 H NMR (300 MHz, DMSO), δ / ppm: 8.30-8.21 (2H), 8.13-8.04 (2H), 8.03-7.81 (2H).

[0023] Ms ( m / z ): 366 (M + )

example 2

[0024] Example 2: Synthesis of 2,7-dibromo9,10-dihydroxyphenanthrene

[0025]

[0026] Under reflux, add 10 mL of concentrated hydrochloric acid in batches to 50 mL of glacial acetic acid solution containing 3.66 g of 2,7-dibromophenanthrenequinone and 4 g of Sn, continue to reflux for 1 h, evaporate most of the glacial acetic acid, and pour the rest Pour into water, filter, wash with water, and dry to obtain 3.50 g flesh red 2,7-dibromo9-10-dihydroxyphenanthrene, with a purity greater than 98% and a yield of 96%.

[0027] 1 H NMR (300 MHz, CDCl 3 ) , δ / ppm: 8.32-8.31 ( 2H ), 7.85-7.84 ( 4H ).

[0028] Ms ( m / z ): 368 (M + ).

example 3

[0029] Example 3: Synthesis of 2,7-dibromo-9-hydroxyl-10-p-tolylphenanthrene

[0030]

[0031] Add 3.70 g of 2,7-dibromo9-10-dihydroxyphenanthrene and a catalytic amount of trifluoromethanesulfonic acid to 20 mL of toluene as a solvent, heat to reflux for 2 h, wash the reaction mixture with water, evaporate the solvent, add an appropriate amount of THF, and filter. The THF was distilled off to give 3.98 g of a gray solid. The purity is greater than 98%, and the yield is 90%.

[0032] 1 H NMR (300 MHz, CDCl 3 ), δ / ppm: 8.51-8.50 ( 1H ), 8.48-8.41 ( 2H ), 7.78-7.75 ( 1H ), 7.57-7.54 ( 1H ), 7.52-7.51 ( 1H ), 7.46-7.43 ( 2H ), 7.31- 7.29 ( 2H ), 5.55 ( 1H ), 2.50 ( 3H ).

[0033] Ms(m / z): 442 (M + ).

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Abstract

The invention discloses a series of 2,7-dibromo-9-hydroxyl phenanthrene derivatives with the following structural formula and a preparation method thereof, belonging to the field of organic chemical synthesis. The synthesis is realized by reacting 2,7-dibromo-9,10-dihydroxyl phenanthrene with an aromatic compound in the presence of a catalyst. R represents phenyl, C1-5 alkyl substituted phenyl or biphenyl. Since the sites 2, 7 and 9 of the phenanthrene derivatives are substituted and a large group is introduced to the site 10, the intermolecular accumulation can be effectively reduced, the derivatives obtain excellent electrochemical performance and high thermal stability, the blue luminescence property is improved, and the molecular dissolubility is also improved. The preparation technology is simple, the raw materials are easily available, the yield is high, and the derivatives are easy to purify and expected to be industrially applied to organic electroluminescence materials.

Description

technical field [0001] The invention relates to phenanthrene derivatives and a preparation method thereof, in particular to a class of 2,7-dibromo-9-hydroxyphenanthrene derivatives and a production method thereof, belonging to the field of organic synthesis. Background technique [0002] Organic electroluminescent materials are expected to become a new generation of flat panel display due to their characteristics such as a wide range of material selection, low energy consumption, high efficiency and luminous brightness, ultra-thin, full curing, fast response, active light emission, and large-area flexible display. As the core component of technology, it has become one of the research hotspots in the field of organic electronics and optoelectronic information. In organic light-emitting diodes, in order to realize large-area full-color display, there must be stable primary colors of red, green and blue. However, only red and green have the luminous efficiency and lifetime nec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/40C07C37/11C09K11/06
Inventor 段显英魏梅林代本才李书静张豫黎朱向珺郭利兵
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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