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1,3-bis(9-phenylfluorene)-benzanthracene derivative and preparation method thereof

A derivative, the technology of benzanthracene, which is applied in the field of 1,3-bis(9-phenylfluorene)-benzanthracene derivatives and its preparation, can solve the problem of insufficient thermal stability, damage to thin film devices, and luminous efficiency. Problems such as color purity and film-forming performance need to be improved to achieve excellent thermal stability, high luminous efficiency, and low raw material cost

Inactive Publication Date: 2012-02-22
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the thermal stability of AND is not good enough, and it is easy to gather crystals and destroy thin film devices.
Introducing a large substituent group at the 9,10-position of anthracene can inhibit its crystallization and improve its film-forming properties and thermal stability, such as introducing fluorene or spirofluorene on the molecular structure of anthracene (Shen, W.J.; Dodda, R.Chem.Mater.2004, 16, 930) or tetraphenyl silicon core (Lyu, Y.Y.; Kwak, J.Adv.Mater.2008, 20, 2720) can improve its thermal stability, but its luminous efficiency and color Purity and film-forming performance need to be improved

Method used

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  • 1,3-bis(9-phenylfluorene)-benzanthracene derivative and preparation method thereof
  • 1,3-bis(9-phenylfluorene)-benzanthracene derivative and preparation method thereof
  • 1,3-bis(9-phenylfluorene)-benzanthracene derivative and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1) Under nitrogen protection, add 15g (0.074mol) of isophthaloyl chloride, 20.7g (0.155mol) of anhydrous aluminum trichloride and 100mL of bromobenzene into a 250ml three-neck flask, stir at room temperature for 8 hours, then heat Continue stirring at 90°C for 2 hours, pour into ice methanol after cooling, and filter to obtain 31.4 g of white 1,3-di-p-bromobenzoylbenzene (compound 1) as a solid, with a yield of 95.3%.

[0029] Identification of compound 1

[0030] Mass Spectrum: [MS(EI)] m / z: C20H12Br2O2 Theoretical 444.1, Actual Measured: 444.

[0031] Proton nuclear magnetic spectrum: 1H-NMR (400MHz, CDCl3) δ (ppm): 8.13 (s, 1H), 8.01-7.99 (d, J=8Hz, 2H), 7.70-7.64 (m, 9H).

[0032] 13C NMR (400MHz, CDCl3, δ): 195.9, 194.8, 138.1, 137.7, 137.5, 137.0, 135.7, 133.9, 133.7, 133.5, 133.1, 132.0, 131.7, 131.2, 131.0, 130.0, 128.9, 128.7, 128.3.

[0033] 2) Under the condition of nitrogen protection, add 3.495g (15mmol) of 2-bromobiphenyl and 50ml of tetrahydrofuran (TH...

Embodiment 2

[0045] 1) with step 1) among the embodiment 1;

[0046] 2) with step 2) in embodiment 1;

[0047] 3) Under nitrogen protection conditions, add 1,3-bis(9-p-bromophenylfluorene)benzene (compound 2) 0.716g (1mmol), 10-phenylanthracene-9-boronic acid pina to a 150ml three-necked flask Esters 0.761g (2mmol), Pd (PPh 3 ) 4 0.035g (0.03mmol), 60ml of toluene and 20ml of 2 moles per liter of potassium carbonate aqueous solution were stirred and refluxed for 24 hours, and the crude product was purified by silica gel chromatography (eluent-petroleum ether / dichloromethane 6: 1v / v) , 0.952 g of white 1,3-bis(9-phenylfluorene)-phenylbiphenylanthracene solid (compound B) was obtained with a yield of 89%.

[0048] Identification of Compound B

[0049] Mass Spectrum: MS (MADLI-TOF): m / z (M+H) + The theoretical value of C84H54 is 1062.42; the actual measured value is 1062.7.

[0050] Proton nuclear magnetic spectrum: 1H NMR (400MHz, CDCl3, δ): 7.848-7.830 (d, J=7.2Hz 4H), 7.788 (s, 1H), ...

Embodiment 3

[0054] 1) with step 1) among the embodiment 1;

[0055] 2) with step 2) in embodiment 1;

[0056] 3) Under nitrogen protection conditions, add 1,3-bis(9-p-bromophenylfluorene)benzene (compound 2) 0.716g (1mmol), 10-naphthyl anthracene-9-boronic acid pinazone into a 150ml three-necked flask Esters 0.861g (2mmol), Pd (PPh 3 ) 4 0.035g (0.03mmol), 60ml of toluene and 20ml of 2 moles per liter of potassium carbonate aqueous solution were stirred and refluxed for 24 hours, and the crude product was purified by silica gel chromatography (eluent-petroleum ether / dichloromethane 6: 1v / v) , 0.911 g of white 1,3-bis(9-phenylfluorene)-benzonaphthylanthracene solid (Compound C) was obtained with a yield of 78%.

[0057] Identification of Compound C

[0058] Mass Spectrum: MS (MADLI-TOF): m / z (M+H) + C92H58, theoretical value 1162.45; actual measured value, 1162.8.

[0059] Proton nuclear magnetic spectrum: 1H NMR (400MHz, CDCl3, δ): 8.057-8.036 (d, J = 8.2Hz, 2H), 8.006-7.985 (d, J =...

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Abstract

The invention relates to 1,3-bis(9-phenylfluorene)-benzanthracene derivatives and a preparation method thereof. The chemical structure of the 1,3-bis(9-phenylfluorene)-benzanthracene derivative provided by the present invention is shown in formula I, wherein, R is a hydrogen atom, phenyl or naphthyl. In the present invention, 4-bromobenzoylbenzene is obtained through the Pay-Craft acylation of isophthaloyl chloride, and then 4-bromobenzoylbenzene is reduced-cyclized with 2-bromobiphenyl to obtain di-9 (4-bromophenyl)fluorenebenzene, and finally Suzuki coupling of bis-9(4-bromophenyl)fluorenebenzene with anthracene boronate to give 1,3-bis(9-phenylfluorene)-phenylene Anthracene derivatives. The invention has the advantages of low cost, simple synthesis route, high yield, high product fluorescence emission efficiency, good thermal stability, film-forming property and shape stability, and the like. Formula I

Description

technical field [0001] The invention relates to a blue-light-emitting 1,3-bis(9-phenylfluorene)-benzanthracene derivative and a preparation method thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have achieved rapid development since they were reported in 1987 (C.W.Tang, S.A. VanSlyke, Appl. Phys. Lett. 1987, 51, 913). Its potential use is as a full-color flat-panel display and white solid-state lighting. Among the three primary colors, green light and red light organic materials have reached or approached the practical application level, but the development of blue light organic materials is relatively slow due to its intrinsic reason, that is, a wide band gap. In addition, due to the high radiant energy of blue light, the interaction between emission groups can easily cause the red shift and broadening of the spectrum, so it is not easy to obtain stable and high-efficiency pure blue light. [0003] Anthracene and its derivatives are favored in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/567C07C1/32C09K11/06H01L51/54
Inventor 刘云圻叶尚辉狄重安吕琨吴卫平杜春燕刘颖于贵
Owner INST OF CHEM CHINESE ACAD OF SCI
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