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Benzocarbazole derivatives and organic light-emitting device thereof

A technology of benzocarbazole derivatives, applied in the field of benzocarbazole derivatives and organic electroluminescent devices

Inactive Publication Date: 2018-09-28
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, as far as the actual needs of the current OLED display lighting industry are concerned, ther...

Method used

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  • Benzocarbazole derivatives and organic light-emitting device thereof
  • Benzocarbazole derivatives and organic light-emitting device thereof
  • Benzocarbazole derivatives and organic light-emitting device thereof

Examples

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preparation example Construction

[0060] The preparation method of the benzocarbazole derivatives of the present invention, the specific synthetic route is as follows:

[0061]

[0062] Wherein, X is selected from O, S or CY 1 Y 2 , Y 1 , Y 2 One of independently selected from substituted or unsubstituted C1-C4 aliphatic groups, substituted or unsubstituted C6-C12 aryl groups; X 1 、X 2 、X 3 、X 4 independently selected from CH or N; R 1 , R 2 , R 3 , R 4 independently selected from hydrogen, deuterium, halogen, cyano, C1-C12 aliphatic, substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C4-C60 heteroaryl; Ar is selected from substituted or Unsubstituted C6-C60 aryl or substituted or unsubstituted C4-C60 heteroaryl.

[0063] Using compound A as the starting material, first undergo Suzuki coupling reaction with boronic acid compound BH-1 or BH-2 to obtain intermediate B-1 or B-2; then undergo ring closure reaction to obtain intermediate C-1 or C- 2; react with a bromide contain...

Embodiment 1

[0069] Embodiment 1: the preparation of intermediate B

[0070]

[0071] Preparation of intermediate B-1: 15.12g (60mmol) 6-bromo-5-nitroisoquinoline, 16.91g (50mmol) 6-boronic acid-7,7-dimethylbenzo[C]fluorene, 4.99 g (4.32mmol) tetrakis (triphenylphosphine) palladium was added in 500ml of tetrahydrofuran, then 250ml of aqueous solution containing 12.44g (90mml) of potassium carbonate was added, and the reaction was refluxed for 24 hours. After the reaction, it was washed with water and methanol, and purified by column chromatography to obtain 18.33 g (44 mmol) of intermediate B-1 with a yield of 88%.

[0072] Intermediate B-2 to Intermediate B-16 can also be prepared by the above method.

Embodiment 2

[0073] Embodiment 2: the preparation of intermediate C

[0074]

[0075] Preparation of Intermediate C-1: Dissolve 12.49g (30mmol) of Intermediate B-1 in 150ml of o-dichlorobenzene, add 6.23g (37.5mmol) of triethyl phosphite, and react at 150°C for 24 hours. After cooling and suction filtration, the organic solvent in the filtrate was distilled off under reduced pressure, and the obtained residue was purified by column chromatography to obtain 12.94 g (26.7 mmol) of intermediate C-1 with a yield of 89%.

[0076] Intermediate C-2 to Intermediate C-16 can also be prepared by the above method.

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Abstract

The invention provides a benzocarbazole derivatives and an organic light-emitting device thereof and relates to the technical field of organic optoelectronic materials. The compounds have simple preparation method and are prepared from easy-to-obtain raw materials, have good stability and high carrier transmission efficiency. When being applied to OLEDs as a main material, the compounds can effectively reduce driving voltage, increase light-emitting efficiency of the devices and prolong service life of the devices. The compounds are a type of organic electroluminescence material having excellent performances.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a benzocarbazole derivative and an organic electroluminescent device. Background technique [0002] Organic electroluminescence refers to the use of organic materials to convert electrical energy into light energy. Organic electroluminescent devices using organic electroluminescence usually include an anode, a cathode, and an organic material layer between the anode and the cathode. Organic electroluminescent device (OLED) technology can be used to manufacture new display products as well as new lighting products. It is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has a wide application prospect. Organic materials used in organic electroluminescent devices can be divided into light-emitting materials and charge injection transport materials according to different uses, for example, hole injection materials, hol...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00C07D495/14C07D491/147C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D471/04C07D491/147C07D495/14C07D519/00C09K2211/1088C09K2211/1092C09K2211/1007C09K2211/1011C09K2211/1029H10K85/623H10K85/622H10K85/624H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/00
Inventor 周雯庭蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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