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Dibenzosuberan enone derivatives and preparation method therefor and application thereof

A technology of dibenzocycloheptenone and its derivatives, which is applied in the field of novel dibenzocycloheptenone derivatives and their preparation and application, can solve problems such as cis-trans configurational isomerization, achieve optimal performance, High thermal stability, good film-forming effect

Inactive Publication Date: 2015-11-04
UNIV OF SCI & TECH BEIJING +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that functionalized aromatic amines have many applications, for example, trans-4,4-bis(diarylamino)stilbene derivatives are excellent light-emitting materials (M. Rumi, J.E. Ehrlich, A.A. Heikal, et al . Journal of the American Chemistry Society, 2000, 122: 9500; J.S. Yang, K.L. Liau, C.M. Wang, et al. Journal of the American Chemistry Society, 2004, 126: 12325.), but due to its structural characteristics, it is easy to lead to Reverse isomerization occurs, which limits the application of such materials

Method used

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  • Dibenzosuberan enone derivatives and preparation method therefor and application thereof
  • Dibenzosuberan enone derivatives and preparation method therefor and application thereof
  • Dibenzosuberan enone derivatives and preparation method therefor and application thereof

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Experimental program
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Effect test

Embodiment 1

[0038] Synthesis of 3,7-bis-(4-dianilinobenzene)-dibenzocyclohepten-5-one (DBHO-TPA): 3,7-Dibromodibenzo[a,d]cycloheptenene -5-ketone (2) (49.14mg, 0.135mmol) and 4-boronate triphenylamine (3) (100mg, 0.27mmol) were dissolved in tetrahydrofuran, and then 2M K was added 2 CO 3 Adjust the pH to 8. Then the whole system is evacuated and filled with nitrogen, and under nitrogen condition, Pd(PPh 3 ) 4 (7.8 mg), and the mixed system was stirred under reflux at 70°C for 48 hours. After the reaction was finished, the solvent was removed under reduced pressure, dichloromethane was added to dissolve, and the inorganic salt was removed by extraction with NaCl salt solution. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was removed by rotary evaporation. The crude product was subjected to silica gel column chromatography ( Petroleum ether-ethyl acetate) to obtain 57 mg of a yellow solid product (DBHO-TPA), with a yield of 61%. The syntheti...

Embodiment 2

[0042] Synthesis of 3,7-di-diphenylamino-dibenzocyclohepten-5-one (DBHO-DPA): Compound 3,7-dibromodibenzo[a,d]cyclohepten- 5-ketone (2) (245mg, 0.68mmol) and diphenylamine (230mg, 1.36mmol) were dissolved in toluene, and sodium tert-butyloxide (146.4mg, 1.52mmol) was added thereto, filled with nitrogen, and stirred at room temperature for half After hours, add Pd 2 (dba) 3 (19.55mg, 0.03mmol) and P( t -Bu) 3 (0.03 mmol), heated to reflux at 100° C. for 16 hours under a nitrogen atmosphere. After the reaction, the solvent was removed under reduced pressure, ethyl acetate was added to dissolve, NaCl salt solution was extracted, and the organic phase was dried with anhydrous magnesium sulfate. Through silica gel column chromatography (petroleum ether-ethyl acetate), 122 mg of a yellow solid product (DBHO-DPA) was obtained, with a yield of 33%. The synthetic route of DBHO-DPA is shown in Table 1.

[0043] The structural formula is as follows:

[0044] .

Embodiment 3

[0046] Synthesis of 3,7-di-carbazole-9-benzocyclohepten-5-one (DBHO-C): Compound 3,7-dibromodibenzo[a,d]cyclohepten-5- Ketone (2) (245mg, 0.68mmol) and carbazole (227mg, 1.36mmol) were dissolved in toluene, then sodium tert-butyloxide (146.4mg, 1.52mmol) was added, filled with nitrogen, and stirred at room temperature for half an hour , join Pd 2 (dba) 3 (19.55mg, 0.03mmol) and P( t -Bu) 3 (0.03mmol), heated to reflux at 100°C for 16 hours under a nitrogen atmosphere. After the reaction, the solvent was removed under reduced pressure, ethyl acetate was added to dissolve, NaCl salt solution was extracted, and the organic phase was dried with anhydrous magnesium sulfate. Through silica gel column chromatography (petroleum ether-ethyl acetate), 200 mg of a yellow solid product (DBHO-C) was obtained, with a yield of 87.5%. The synthetic route of DBHO-C is shown in Table 1

[0047] The structural formula is as follows:

[0048] .

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PUM

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Abstract

The present invention belongs to the field of organic semiconductor materials and devices, and relates to novel dibenzosuberan enone derivatives and a preparation method therefor and an application thereof. The general structural formula of the dibenzosuberan enone derivatives is as shown in the specification. According to the method, dibenzosuberan enone is used as a skeleton structure, and a substituent with a hole transport property substitutes hydrogen in the skeleton structure through coupling reaction to prepare the dibenzosuberan enone derivatives; the prepared dibenzosuberan enone derivatives are used as an organic semiconductor layer to prepare a blue and green light emitting organic electroluminescent device. In the preparation method, the substituent with the hole transport property can improve thermal stability of the material and performance of the electroluminescent device, and the blue and green light emitting organic electroluminescence device is obtained by using the material as the light emitting layer.

Description

technical field [0001] The invention belongs to the field of organic semiconductor materials and devices, and relates to novel dibenzocycloheptenone derivatives and their preparation and application. Background technique [0002] Organic electroluminescent (OLED) devices have attracted widespread attention due to their great application potential in the fields of full-color flat panel displays and solid-state light sources, among which the performance of light-emitting materials is an important factor affecting the application of organic electroluminescent devices. In order to obtain high-efficiency organic electroluminescent devices, organic light-emitting materials are generally required to have high thermal stability, excellent film-forming properties, high carrier injection or transport capabilities, appropriate energy levels, and excellent light-emitting characteristics. Organic molecules with conjugated structures usually have good luminescent properties and carr...

Claims

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Application Information

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IPC IPC(8): C07C225/22C07C221/00C07D209/86C09K11/06H01L51/54
Inventor 王丽萍王莉敏于贵
Owner UNIV OF SCI & TECH BEIJING
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