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Preparation method of fluorene-containing polycyclic aromatic hydrocarbon disc-shaped liquid crystal compound

A technique for discotic liquid crystal and compound, applied in the field of discotic liquid crystal compound and preparation thereof

Inactive Publication Date: 2019-06-07
SICHUAN NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] In the past 20 years, the research on organic or polymer light-emitting diodes (OLEDs / PLEDs) has mainly focused on industrial aspects and academic aspects; among them, a major problem is that the luminescence of condensed light-emitting polymers for LEDs is aggregation-induced concentration Quenched state, which is a kind of red light-emitting material that is highly valued, aggregation-induced concentration quenched state is considered to be one of the main problems solved by polyfluorene derivatives, and this type of light-emitting polymer is the most studied, standing From a chemical point of view, such problems may be solved by designing luminescent materials with steric hindrance effects; however, the related boronic esters of fluorene expand the functional materials formed by conjugated coplanar planes by coupling with monobrominated biphenyls and then closing the ring. Reports are still in the minority

Method used

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  • Preparation method of fluorene-containing polycyclic aromatic hydrocarbon disc-shaped liquid crystal compound
  • Preparation method of fluorene-containing polycyclic aromatic hydrocarbon disc-shaped liquid crystal compound
  • Preparation method of fluorene-containing polycyclic aromatic hydrocarbon disc-shaped liquid crystal compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] The compound provided in this example is the compound of general formula (I), which is L51.

[0108]Add compound 3-a (100mg, 0.08mmol) and dichloromethane (40ml) into a 150ml round bottom flask, take a 25ml small beaker, add 4ml nitromethane, ferric chloride (68.14mg, 0.42mmol) , react at room temperature, track the reaction every 15 minutes, when the 3-a reaction is complete and new products are produced, add methanol to stop the reaction, extract with dichloromethane, dry the organic phase with MgSO4, filter, and spin dry the organic solvent ; Through silica gel column chromatography (eluent: V dichloromethane: V petroleum ether = 1:1), recrystallization with ethanol and ethyl acetate gave white solid L51 (93.5 mg, yield 93.8%).

[0109] 1H NMR(CDCl3, TMS, 400 MHz), δ:9.00(s, 2H, ArH), 8.52(s, 2H,ArH), 8.29(s, 2H, ArH), 8.11(s, 2H, ArH) ), 7.87(s, 4H, ArH), 4.39(t, J = 5.6Hz, 4H, OCH2), 4.29(t, J = 3.6 Hz, 12H, OCH2), 1.97-2.07(m, 16H, CH2), 1.84(s, 6H, 2CH3), 1.49-...

Embodiment 2

[0114] The compound provided in this example is the compound of general formula (I), which is L58.

[0115] Add compound 3-b (180mg, 0.13mmol) and dichloromethane (50ml) into a 150ml round bottom flask, take a 25ml small beaker, add 5ml nitromethane, ferric chloride (105.7mg, 0.65mmol) , react at room temperature, track the reaction every 15 minutes, when the 3-b reaction is complete and new products are produced, add methanol to stop the reaction, extract with dichloromethane, dry the organic phase with MgSO4, filter, and spin dry the organic solvent ; Through silica gel column chromatography (eluent: V dichloromethane: V petroleum ether = 1:1.5), recrystallization with ethanol and ethyl acetate gave white solid L58 (143.6 mg, yield 80.0%).

[0116] 1H NMR(CDCl3, TMS, 400 MHz), δ:9.00(s, 2H, ArH), 8.41(s, 2H, ArH), 8.30(s, 2H, ArH), 8.12(s, 2H, ArH) ), 7.89(s, 4H, ArH), 4.31(t, J = 6.8Hz, 16H, OCH2), 2.28(t, J = 7.2 Hz, 4H, 2CH2), 1.94-2.05(m, 16H, CH2), 1.48-1.62(m, 40H, C...

Embodiment 3

[0121] The compound provided in this example is the compound of general formula (I), which is L81.

[0122] Add compound 3-c (200mg, 0.13mmol) and dichloromethane (60ml) into a 150ml round bottom flask, take a 25ml small beaker, add 5ml nitromethane, ferric chloride (106.6mg, 0.66mmol) , react at room temperature, track the reaction every 15 minutes, when the 3-c reaction is complete and new products are produced, add methanol to stop the reaction, extract with dichloromethane, dry the organic phase with MgSO4, filter, and spin dry the organic solvent ; Through silica gel column chromatography (eluent: V dichloromethane: V petroleum ether = 1:2), recrystallization with ethanol and ethyl acetate gave white solid L81 (160 mg, yield 80.4%).

[0123] 1H NMR(CDCl3, TMS, 400 MHz), δ:9.00(s, 2H, ArH), 8.52(s, 2H,ArH), 8.30(s, 2H, ArH), 8.12(s, 2H, ArH) ), 7.88(s, 4H, ArH), 4.32(t, J = 6.4Hz, 16H, OCH2), 1.94-2.04(m, 16H, CH2), 1.84(s, 6H, 2CH3), 1.33-1.66(m , 80H,CH2), 0.91(t, J = ...

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Abstract

The invention discloses a disc-shaped liquid crystal compound containing a fluorene luminescent group. Researches show that the compounds are simple and convenient in synthesis, and are mainly obtained by Suzuki coupling and then ring closure reactions. Some monobrominated biphenyls are used as raw materials and can be subjected to Suzuki coupling with borate; therefore, the required disc-shaped liquid crystal compound containing the fluorene luminescent group is synthesized through simple substitution, coupling and ring closing reactions. The synthetic route of the compound is short. Fluoreneis used as a good light-emitting element, and the compound combines a liquid crystal element and a light-emitting element, so that the disc-shaped liquid crystal compound containing the fluorene light-emitting group and having the liquid crystal property and the light-emitting property is synthesized. According to the invention, a stable hexagonal columnar phase and a nematic phase can be formedin a very wide temperature range. The compound is a good mesocrystal, has a good luminescence property, and can be used as a luminescent material with a quantum yield of about 75%.

Description

technical field [0001] The invention relates to a discotic liquid crystal compound containing a fluorene luminescent group and a preparation method thereof. Background technique [0002] At present, discotic liquid crystals are a unique class of materials with remarkable electrical and photoconductive properties and can form nano-microstructures through self-assembly. It is a planar discoid molecule with π-bond conjugation, which was mainly used in phase compensation films in the early days. Due to its one-dimensional intermolecular columnar packing, it can self-assemble into a columnar structure, especially a hexagonal columnar phase; this is a The three-dimensional charge carrier system offers unique possibilities; the interaction of electrons and the influence of electron mobility rate make the stacking period along the column much shorter than the distance between columns. Therefore, discotic liquid crystals are considered to be promising organic semiconductors in the f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/32C09K11/06C07C41/18C07C43/21
Inventor 杨瑶赵可孝赵可清胡平汪必琴
Owner SICHUAN NORMAL UNIVERSITY
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