2,7-dibromide-9,10 substituted-phenanthrene derivatives

A derivative, 10- technology, applied in the field of 2, phenanthrene derivatives and their preparation, can solve the problems of large solvent consumption and poor solubility, and achieve the effects of improved solubility, easy purification, and improved blue luminescence performance

Inactive Publication Date: 2013-08-21
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The invention patent 201210287739.6 previously applied by the inventor discloses 2,7-dibromo-9-hydroxyphenanthrene derivatives. Although they have good thermal stability and spectral stability, they are found to have poor solubility during use. The solvent consumption is large, and due to the presence of hydroxyl active hydrogen in the molecular structure, it is not conducive to further introducing other groups at the 2 and 7 positions, which limits its application

Method used

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  • 2,7-dibromide-9,10 substituted-phenanthrene derivatives
  • 2,7-dibromide-9,10 substituted-phenanthrene derivatives
  • 2,7-dibromide-9,10 substituted-phenanthrene derivatives

Examples

Experimental program
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Effect test

example 1

[0019] Example 1: Synthesis of 2,7-dibromo-9,10-diethoxyphenanthrene

[0020] (1) 2,7-Dibromophenanthrenequinone

[0021]

[0022] Under full stirring, 17.95 g of NBS was added to 98% concentrated sulfuric acid containing 10 g of 9,10-diphenanthrenequinone by mass, and stirred at room temperature for 3 h, then the mixture was poured onto ice cubes, the organic matter was filtered, and washed with cold water. The crude product was recrystallized with DMSO to obtain 13 g orange-red 2,7-dibromophenanthrenequinone, yield: 75%.

[0023] 1 H NMR (300 MHz, DMSO), δ / ppm: 8.30-8.21 (2H), 8.13-8.04 (2H), 8.03-7.81 (2H).

[0024] Ms ( m / z ): 366 (M + )

[0025] (2) 2,7-dibromo-9,10-dihydroxyphenanthrene

[0026]

[0027] Under reflux, add 10 mL concentrated hydrochloric acid in batches to 50 mL glacial acetic acid solution containing 3.66 g 2,7-dibromophenanthrenequinone and 4 g Sn, continue reflux for 1 h, distill most of the glacial acetic acid, and pour the rest Pour into...

example 2

[0035] Example 2: Synthesis of 2,7-dibromo-9,10-dipropoxyphenanthrene

[0036]

[0037] Add 2,7-dibromo9,10-dihydroxyphenanthrene (2.0 g, 5.4 mmol) and a catalytic amount of trifluoromethanesulfonic acid in 20 mL of propanol as a solvent, heat to reflux for 2 h, distill off part of the solvent and concentrate the reaction mixture. It was then washed with water and recrystallized from methanol to obtain 1.9 g of gray solid, M.P., 124.9 °C (by DSC), with a purity greater than 95 % and a yield of 78 %.

[0038] 1 H NMR (400 MHz, CDCl 3 ), δ / ppm: 8.43-8.40 (m, 2H ), 7.71-7.64 (m, 4H ), 3.37–3.57 (m, 4H), 1.60–1.55 (m, 4H), 0.87 (t, 6H, J= 7.36 Hz). 13CNMR (CDCl 3 , 400MHz, ppm) δ 143.0, 131.6, 130.5, 125.9, 124.6, 122.6, 120.9, 77.1, 22.6, 10.4.

[0039] Ms(m / z): 453 (M + ).

example 3

[0040] Example 3: Solubility Experiment

[0041] Comparing the solubility of 2,7-dibromo-9-phenanthrene derivatives in patent 201210287739.6 with that of 2,7-dibromo-9,10-phenanthrene derivatives in this patent, the results are as follows:

[0042] compound Solubility(g / mL) 2,7-Dibromo-9-hydroxy-10-p-tolylphenanthrene 0.7 Synthesis of 2,7-dibromo-9-hydroxy-10-phenylphenanthrene 0.4 2,7-Dibromo-9-hydroxy-10-p-xylphenanthrene 0.8 Synthesis of 2,7-dibromo-9-hydroxy-10-p-biphenylphenanthrene 0.2 2,7-Dibromo-9,10-diethoxyphenanthrene 2 2,7-Dibromo-9,10-dipropoxyphenanthrene 3

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Abstract

The invention discloses a series of 2,7-dibromide-9,10 substituted-phenanthrene derivatives having a structural formula as shown in the specification and a preparation method thereof, belonging to the field of organic chemical synthesis. Synthesis of the derivatives is realized by reacting 2,7-dibromide-9,10-dihydroxyl phenanthrene with alcohol compounds in the presence of a catalyst. According to the phenanthrene derivatives, substitution is carried out on sites 2,7,9 and 10, intermolecular accumulation can be effectively reduced, excellent electrochemical performance and high thermal stability are achieved, blue luminescence property of the phenanthrene derivatives is improved, and molecular dissolving property is also improved. A preparation process is simple, raw materials are available, yield is high, purification is easy, industrialization is hopeful, and the phenanthrene derivatives can be applied to organic electroluminescent materials. In a general formula, R1 and R2 are C1-C3 alkyls, and substituent groups are the same.

Description

technical field [0001] The invention relates to phenanthrene derivatives and a preparation method thereof, in particular to a class of 2,7-dibromo-9,10-substituted-phenanthrene 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 lif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C07C41/09
Inventor 郭利兵郝二军崔风华陈波刘铁良刘鹏举侯益民
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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