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Fluorenocarbazole derivative, preparation method and applications thereof

A technology for fluorenocarbazole derivatives, which is applied in the field of fluorenocarbazole derivatives, their preparation and application, can solve problems such as constraints and difficult synthesis, and achieve high product yield and purity, and uniform product yield and purity. , synthesize simple effects

Active Publication Date: 2019-08-16
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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  • Fluorenocarbazole derivative, preparation method and applications thereof
  • Fluorenocarbazole derivative, preparation method and applications thereof
  • Fluorenocarbazole derivative, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1: the synthesis of compound (1)

[0055] 1a. Synthesis of fluorenocarbazole:

[0056]

[0057] S1. In a 250mL three-necked flask, put 4-bromo-9,9-dimethyl-9H-fluorene (8.20g, 30 mmol), 2-chloroaniline (4.59g, 36mmol), triphenylphosphine (0.04 g, 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), 70°C The reaction was carried out for 1-4 hours, and the reaction of 4-bromo-9,9-dimethyl-9H-fluorene was monitored by the liquid phase. The reaction was quenched by adding water, separated, the organic phase was concentrated, rinsed with petroleum ether through a silica gel column, and rinsed with petroleum ether. The washing 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%.

[0058] S2. In a 100mL three-necked flask, put t...

Embodiment 2

[0065] Embodiment 2: the synthesis of compound (4)

[0066] 1a. Synthesis of fluorenocarbazole:

[0067] Synthetic process is with the synthetic process of 1a in embodiment 1

[0068] 1b. Synthesis of 12-(3'-bromo-[1,1'-biphenyl]-3-yl)-fluorenocarbazole

[0069]

[0070] In Example 1, 4-bromo-4'-iodo-1,1'-biphenyl (3.59g, 10mmol) was replaced by 3-bromo-3'-iodo-1,1'-biphenyl (3.59g, 10mmol), other synthetic processes are the same as the synthetic process of 1b in Example 1 to obtain white powdery 12-(3'-bromo-[1,1'-biphenyl]-3-yl)-fluorenocarbazole 4.39g, yield 85%, purity 99.09%.

[0071] 1c. Synthesis of compound (4)

[0072] 5mmol) was replaced by 12-(3'-bromo-[1,1'-biphenyl]-3-yl)-fluorenocarbazole (2.57g, 5mmol), and other synthetic processes were the same as those of 1c in Example 1 , 2.75 g of compound (4) was obtained as a white powder, with a yield of 91% and a purity of 99.18%.

[0073] Mass spectrometer MALDI-TOF-MS (m / z) = 602.7805, theoretical molecular...

Embodiment 3

[0074] Embodiment 3: the synthesis of compound (6)

[0075] 1a. Synthesis of fluorenocarbazole:

[0076] Synthetic process is with the synthetic process of 1a in embodiment 1

[0077] 1b. Synthesis of 12-(3'-bromo-[1,1'-biphenyl]-4-yl)-fluorenylcarbazole

[0078]

[0079] In Example 1, 4-bromo-4'-iodo-1,1'-biphenyl (3.59g, 10mmol) was replaced by 3-bromo-4'-iodo-1,1'-biphenyl (3.59g, 10mmol), other synthetic processes are the same as the synthetic process of 1b in Example 1 to obtain white powdery 12-(3'-bromo-[1,1'-biphenyl]-4-yl)-fluorenocarbazole 4.33g, yield 84%, purity 99.10%.

[0080]

[0081] In Example 1, 12-(4'-bromo-[1,1'-biphenyl]-4-yl)-fluorenocarbazole (2.57g, 5mmol) was replaced by 12-(3'-bromo-[ 1,1'-biphenyl]-4-yl)-fluorenocarbazole (2.57g, 5mmol), diphenylamine (1.69g, 10mmol) was replaced by N-phenyl-[1,1'-biphenyl]- 4-Amine (2.45g, 10mmol), and the other synthesis process was the same as that of 1c in Example 1 to obtain 2.95g of white powder compou...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a fluorenocarbazole derivative, a preparation method and applications thereof. According to the present invention, the fluorenocarbazole derivative is a class of hole transporting materials and light emitting layer host materials with excellent electroluminescence, excellent thermal stability, excellentservice life and other excellent comprehensive properties, has characteristics of simple synthesis, high yield and high purity, and can meet the requirements on the performances and the quality of materials in industrial applications.

Description

technical field [0001] The invention belongs to the field of organic synthesis science and technology, in particular to a fluorenocarbazole derivative, its preparation method and application. 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, because small molecule luminescent materials are easy to form agglomerations in solid phase, resulting in fluorescence quenching or red shift...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/94C07D405/12C07D409/12C07D471/04C09K11/06H01L51/50H01L51/54
CPCC07D209/94C07D405/12C07D409/12C07D471/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H10K85/615H10K85/626H10K85/6576H10K85/6574H10K85/6572H10K50/11
Inventor 穆广园庄少卿任春婷徐鹏
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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