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Fluorene carbazole derivative as well as preparation method and application thereof

A technology of fluorenocarbazole and derivatives, which is applied in the field of fluorenocarbazole derivatives and their preparation, can solve the problems of difficult synthesis and constraints, and achieve the expansion of conjugated structure, compact configuration, high thermal stability and electrogenicity. The effect of the characteristic

Active Publication Date: 2019-06-28
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, the steric effect has a great influence on the synthesis of the compound. The 3,6-position of carbazole is activated by the nitrogen atom, and a variety of electrophilic substitution reactions are easy to occur at these two positions. Therefore, the carbazole ring 3, 6, and 9 It is easy to chemically modify the carbazole position to introduce other functional groups, but it is much more difficult to synthesize substitutions at the 1, 2, 7, and 8 positions of carbazole, which restricts the development of carbazole-based organic electroluminescent materials with better performance.

Method used

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  • Fluorene carbazole derivative as well as preparation method and application thereof
  • Fluorene carbazole derivative as well as preparation method and application thereof
  • Fluorene carbazole derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: the synthesis of intermediate fluorenocarbazole

[0049]

[0050] S1. In a 250mL three-necked flask, put 4-bromo-9,9-dimethyl-9H-fluorene (8.20g, 30mmol), 2-chloroaniline (4.59g, 36mmol), triphenylphosphine (0.04g , 0.15mmol), sodium tert-butoxide (8.65g, 90mmol), add 80mL ethanol and 40mL water, under nitrogen atmosphere, add tris(dibenzylideneacetone) dipalladium (0.27g, 0.3mmol), at 70°C Reaction 1-4h, liquid phase monitoring 4-bromo-9,9-dimethyl-9H-fluorene reaction is complete, add water to quench the reaction, separate liquid, concentrate the organic phase, rinse with petroleum ether through a silica gel column, rinse The solution was concentrated to obtain 9.02 g of N-(2-chlorophenyl)-9,9-dimethyl-9H-fluoren-4-amine as a colorless transparent oil, with a yield of 94% and a purity of 99.85%.

[0051] S2. In a 100mL three-necked flask, put the above-mentioned N-(2-chlorophenyl)-9,9-dimethyl-9H-fluorene-4-amine (5.67g, 20mmol), tri-tert-butylphosph...

Embodiment 2

[0052] Embodiment 2: the synthesis of compound (4)

[0053]

[0054] S3. In a 250mL three-necked flask, put the above-mentioned fluorenylcarbazole (4.25g, 15mmol), 5-bromo-2-iodopyridine (5.67g, 20mmol), 18-crown-6 (0.79g, 3mmol), Potassium carbonate (10.36g, 75mmol), add 75mL dimethylacetamide, under nitrogen atmosphere, add cuprous iodide (0.57g, 3mmol), react at 160°C for 4-8h, monitor the completion of the reaction in liquid phase, cool to room temperature, washed with water, filtered, and the filter cake was beaten again with 3-5 times of ethyl acetate, and then heated with a 10:1 ethyl acetate: ethanol mixed solvent to obtain white powdery intermediate 12-( 5-bromopyridin-2-yl)-fluorenocarbazole 5.47g, yield 83%.

[0055] S4. In a 100mL three-necked flask, put the above-mentioned intermediate 12-(5-bromopyridin-2-yl)-fluorenocarbazole (2.20g, 5mmol), 4,4-dimethyldiphenylamine (1.78g, 9mmol), tri-tert-butylphosphine tetrafluoroborate (0.06g, 0.2mmol), sodium tert-but...

Embodiment 3

[0057] Embodiment 3: the synthesis of compound (9)

[0058]

[0059] The 5-bromo-2-iodopyridine (5.67g, 20mmol) in Example 2 was replaced by 4-bromo-4'-iodo-1,1'-biphenyl (7.18g, 20mmol), 4,4-bis Methyldiphenylamine (1.78g, 9mmol) is replaced by diphenylamine (1.52g, 9mmol), and other synthetic processes are the same as in Example 2 (the intermediates of each corresponding step can be different, but other reactants, mol ratios, and reaction conditions are identical ) to obtain 2.50 g of compound (9) in the form of white powder, with a yield of 90%.

[0060] Mass spectrometer MALDI-TOF-MS (m / z) = 602.7803, theoretical molecular weight: 602.7810; Anal.Calcd forC 45 h 34 N 2 (%): C 89.67, H 5.69, N 4.65, Found: C 89.69, H 5.68, N 4.64.

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Abstract

The invention belongs to the fields of organic synthesis science and technology and particularly relates to fluorene carbazole derivative and application thereof. A type of hole transportation materials and efficiency improvement layer materials with excellent compressive properties such has electroluminescence, heat stability and service lives are formed by bridging a specific fluorene carbazoleunit with alkyl substituted or unsubstituted arylamine or aryl phosphate oxygen groups, and the fluorene carbazole derivative can meet the requirements of an industrial layer on the integral performance of devices.

Description

technical field [0001] The invention belongs to the field of organic synthesis science and technology, and specifically relates to a fluorenocarbazole derivative and a preparation method and application thereof. Background technique [0002] Carbazole is an electron-rich nitrogen-containing heterocyclic compound. The electrophilic nitrogen atom of carbazole absorbs electrons on the carbon-carbon double bond through the induction effect, and at the same time has the P-π conjugation effect. Therefore, the carbazole ring has a high The hole mobility and luminous efficiency make its derivatives have potential wide applications in fields such as optoelectronic materials, dyes, medicine, and supramolecular recognition. [0003] Due to the limitation of molecular structure, the molecular thermal stability of monocarbazole compounds is poor, and at the same time, small molecule luminescent materials are easy to form agglomeration in solid phase, which leads to fluorescence quenching...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D209/94C07D401/10C07F9/6558C07F9/572C09K11/06H01L51/50H01L51/54
Inventor 穆广园庄少卿任春婷徐鹏
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD