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A kind of fluorenocarbazole derivative, its preparation method and application

A technology for fluorenocarbazole and derivatives, which is applied in the fields of fluorenocarbazole derivatives, their preparation and application, can solve the problems of restriction and difficult synthesis, and achieves high product yield and purity, and uniform product yield and purity. , synthesizing simple effects

Active Publication Date: 2021-02-02
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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  • A kind of fluorenocarbazole derivative, its preparation method and application
  • A kind of fluorenocarbazole derivative, its preparation method and application
  • A kind of fluorenocarbazole derivative, its preparation method and application

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 time is 1-4h, the liquid phase monitors the completion of the 4-bromo-9,9-dimethyl-9H-fluorene reaction, adding water to quench the reaction, separating the liquids, concentrating the organic phase, rinsing with petroleum ether through a silica gel column, and rinsing 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 the above-mentioned N-(2-chloro...

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), the other synthesis process was the same as that of 1c in Example 1 to obtain 2.95g of white powder compound (...

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Abstract

The invention belongs to the field of organic synthesis technology, in particular to the field of organic synthesis technology, in particular to a fluorenocarbazole derivative and a preparation method and application thereof. The fluorenocarbazole derivatives provided by the present invention are a kind of hole-transporting materials and light-emitting layer host materials with excellent comprehensive properties such as electroluminescence, thermal stability and lifespan, and the synthesis is simple, and the yield and purity are high. It can meet the requirements of material performance and quality 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 Patents(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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