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Electron transport material for organic electroluminescent devices and preparation method of electron transport material

An electron transport material and electroluminescence device technology, applied in the field of electron transport materials and their preparation, can solve the problems of single variety of electron transport materials, difficult to optimize performance, difficult structural design, etc., and achieve high reaction yield and short synthesis route. , material structure design and performance optimization easy effect

Active Publication Date: 2012-05-09
苏州纳凯科技有限公司
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Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the difficulty in designing the structure of 4,7-diaryl-1,10-phenanthroline compounds in the prior art, which leads to the single variety of electron transport materials used in organic electroluminescent devices, The performance is difficult to optimize, and a simple and easy-to-obtain 4,7-diaryl-1,10-phenanthroline electron transport material is provided

Method used

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  • Electron transport material for organic electroluminescent devices and preparation method of electron transport material
  • Electron transport material for organic electroluminescent devices and preparation method of electron transport material
  • Electron transport material for organic electroluminescent devices and preparation method of electron transport material

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Embodiment 1

[0035] Weigh 4,7-dichloro-1,10-phenanthroline (2.49g, 10mmol) and dissolve it in 14mL toluene, pour it into the reactor, then add m-tolylboronic acid (2.85g, 24mmol ), Pd(PPh 3 ) 4 (231mg, 0.2mmol), Na 2 CO 3 (2.1 g, 20 mmol) and 7 mL of water. The above mixture was reacted at 90° C. for 24 hours under the protection of argon. Add water to the reaction solution to terminate the reaction, extract with ethyl acetate, wash the organic layer obtained by the extraction with saturated brine first, then wash with pure water, and finally dry, filter, and spin-dry with a rotary evaporator to obtain the crude product, which is then via CH 2 Cl 2 / THF (5:1) was used as mobile phase column chromatography to obtain 3.00 g of analytically pure final product, yield: 76%. 1 H NMR (400 MHz, CDCl3): δ 9.22 (2H, d, J=4.4 Hz), 7.86 (2H, s), 7.57 (2H, d, J=4.4 Hz), 7.43-7.34 (2H, m), 7.33-7.29 (6H, m), 2.44 (6H, s). The reaction equation of the present embodime...

Embodiment 2

[0039] Weigh 4,7-dichloro-1,10-phenanthroline (2.49g, 10mmol) and dissolve it in 14mL toluene, pour it into the reactor, then add p-phenylboronic acid (4.75g, 24mmol ), Pd(PPh 3 ) 4 (231mg, 0.2mmol), Na 2 CO 3 (2.1 g, 20 mmol) and 7 mL of water. The above mixture was reacted at 90° C. for 24 hours under the protection of argon. Add water to the reaction solution to terminate the reaction, extract with ethyl acetate, wash the organic layer obtained by the extraction with saturated brine first, then wash with pure water, and finally dry, filter, and spin-dry with a rotary evaporator to obtain the crude product, which is then via CH 2 Cl 2 / THF (5:1) was used as mobile phase column chromatography to obtain 3.00 g of analytically pure final product, yield: 76%. 1 H NMR (400 MHz, CDCl3): δ 9.27 (2H, d, J=4.8 Hz), 7.97 (2H, s), 7.77 (4H, m, J=4.8 Hz), 7.69 (4H, m, J=7.6 Hz), 7.65-7.62 (6H, m), 7.52-7.48 (4H, m), 7.42-7.39 (2H, m). The reaction eq...

Embodiment 3

[0043] Weigh 4,7-dichloro-1,10-phenanthroline (2.49g, 10mmol) and dissolve it in 14mL toluene, pour it into the reactor, then add 1-naphthylphenylboronic acid (4.13g, 24mmol), Pd(PPh 3 ) 4 (231mg, 0.2mmol), Na 2 CO 3 (2.1 g, 20 mmol) and 7 mL of water. The above mixture was reacted at 90° C. for 24 hours under the protection of argon. Add water to the reaction solution to terminate the reaction, extract with ethyl acetate, wash the organic layer obtained by the extraction with saturated brine first, then wash with pure water, and finally dry, filter, and spin-dry with a rotary evaporator to obtain the crude product, which is then via CH 2 Cl 2 / THF (5:1) was used as mobile phase column chromatography to obtain 2.6 g of analytically pure final product, yield: 60%. 1 H NMR (400 MHz, CDCl 3 ): δ 9.35 (2H, d, J=4.4 Hz), 7.95-7.89 (4H, m), 7.66 (2H, d, J=4.8 Hz), 7.57-7.53 (2H, m), 7.48-7.43 (4H , m), 7.37-7.29 (4H, m), 7.21 (1H, s), 7.19 (1...

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Abstract

The invention relates to an electron transport material for organic electroluminescent devices and a preparation method of the electron transport material. The preparation method comprises the following steps of taking 4,7-dihalogen-1,10-phenanthroline as a starting material, and carrying out a Suzuki reaction on the starting material and arylboronic acid or arylboronate to obtain 4,7-diaryl-1,10-phenanthroline and derivates thereof as the electron transport material. The method provided by the invention has shorter synthetic route, simpler technology and higher reaction yield, obtains end-products with various types of different substituent groups, and has more easiness in material structure design and performance optimization in comparison with the conventional Skraup preparation method; meanwhile, no highly toxic materials such as arsenic acid and the like are in the reaction process, so that the reaction condition is milder, and the reaction process is safer and more environment-friendly. The preparation method provided by the invention is suitable for laboratorial preparation in gram scale and kilogram scale as well as industrial mass production in ton scale.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to an electron transport material used in an organic electroluminescence device and a preparation method thereof. Background technique [0002] At present, the electron transport material used in organic electroluminescent devices (OLED) is mainly 4,7-diphenyl-1,10-phenanthroline, which is 4,7-diaryl-1,10-phenanthrene One of the roline compounds. The traditional method of synthesizing 4,7-diaryl-1,10-phenanthroline compounds is mainly realized by continuous Skraup reaction (see formula Ⅰ), because the starting material Ar 2 COCH 2 CH 2 The aryl group Ar in Cl has certain limitations in the selection. At present, only simple 4,7-diphenyl-1,10-phenanthroline, 4,7-benzhydryl -1,10-phenanthroline and 4,7-diphenylmethoxy-1,10-phenanthroline and other limited phenanthroline compounds, which make 4,7-diaryl-1,10-phenanthroline The structural design of m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04H01L51/54
Inventor 李宛飞周明刘扬周宇扬王鑫
Owner 苏州纳凯科技有限公司
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