Fluorinated triphenylamine electro-material and application thereof

A technology of triphenylamines and electroluminescent materials, applied in luminescent materials, circuits, photovoltaic power generation, etc., can solve the problem of few blue-violet light-emitting devices, achieve large changes in glass transition temperature range, low turn-on voltage, and simplify devices structure effect

Inactive Publication Date: 2013-01-16
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there are few undoped blue-violet light-emitting devices that can emit wavelengths below 420nm.

Method used

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  • Fluorinated triphenylamine electro-material and application thereof
  • Fluorinated triphenylamine electro-material and application thereof
  • Fluorinated triphenylamine electro-material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: Synthesis of fluorinated triphenylamine material 1:

[0029]

[0030] Under a nitrogen atmosphere, into a 100 mL round bottom flask, mix Na 2 CO 3(2.0M, 15mL), ethanol (10mL) and toluene (30mL), replace nitrogen three times; then add 3mmol tris(4-bromophenyl)amine, 10mmol 2-fluorophenylboronic acid and 0.30mmol tetrakis(triphenylphosphine) ) palladium, replaced nitrogen three times, stirred, heated to reflux, and reacted for 12 hours. The reaction was followed by thin layer chromatography. When the reaction was complete, it was cooled, and 20 mL of water was added to the reaction mixture, extracted three times with dichloromethane, the organic layer was washed with water, and dried over anhydrous sodium sulfate. The organic phase was concentrated, and the pure product 1 was obtained by column chromatography with ethyl acetate and petroleum ether with a yield of 88% (1.39 g). MP: 241°C. 1 H NMR (CDCl 3 , 400MHz): δ7.08-7.17 (m, 3H), 7.24-7.26 (t, 3...

Embodiment 2

[0031] Embodiment 2: Synthesis of fluorinated triphenylamine material 5:

[0032] Under a nitrogen atmosphere, into a 100 mL round bottom flask, mix Na 2 CO 3 (2.0M, 15mL), ethanol (10mL) and toluene (30mL), replace nitrogen three times; then add 5mmol tris(4-bromophenyl)amine, 18mmol 2,4-difluorophenylboronic acid and 0.50mmol tetrakis(triphenyl) Base phosphine) palladium, replace nitrogen three times, stir, heat to reflux, and react for 12 hours. The reaction was followed by thin layer chromatography. When the reaction was complete, it was cooled, and 20 mL of water was added to the reaction mixture, extracted three times with dichloromethane, the organic layer was washed with water, and dried over anhydrous sodium sulfate. The organic phase was concentrated, and the pure product 5 was obtained by column chromatography with ethyl acetate and petroleum ether with a yield of 85% (2.44 g). MP: 162°C. 1 H NMR (CDCl 3 , 400MHz): δ6.88-6.97 (m, 6H), 7.22-7.25 (t, 6H), 7.39-7...

Embodiment 3

[0033] Embodiment 3: Synthesis of fluorinated triphenylamine material 13:

[0034]

[0035] Under a nitrogen atmosphere, into a 100 mL round bottom flask, mix Na 2 CO 3 (2.0M, 15mL), ethanol (10mL) and toluene (30mL), replace nitrogen three times; then add 3mmol tris(4-bromophenyl)amine, 10mmol 3,4,5-fluorophenylboronic acid and 0.30mmol tetrakis( Triphenylphosphine) palladium, replaced nitrogen three times, stirred, heated to reflux, and reacted for 12 hours. The reaction was followed by thin layer chromatography. When the reaction was complete, it was cooled, and 20 mL of water was added to the reaction mixture, extracted three times with dichloromethane, the organic layer was washed with water, and dried over anhydrous sodium sulfate. The organic phase was concentrated, and the pure product 13 was obtained by column chromatography with ethyl acetate and petroleum ether in a yield of 82% (1.56 g). MP: 179°C. 1 H NMR (CDCl 3 , 400MHz): δ7.02-7.04 (d, J=8.8Hz, 3H), 7....

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Abstract

The invention discloses a fluorinated triphenylamine electro-material and an application thereof; according to the material, through the change of the positions and the numbers of hole transporting moieties of strong electron-withdrawing groups of fluorine or trifluoromethyl at periphery of triphenylamine, the energy of the highest occupied molecular orbital, the energy of the lowest unoccupied molecular orbital, the charge transport capacity, photophysical properties and thermal properties of the material are adjusted; thus balance between the injection and transport of holes and electrons is reached; most holes and electrons of the injected device are combined in a luminescent layer; therefore, the device structure is greatly simplified, and the device performance is improved. Meanwhile, through the modification of fluorine or trifluoromethyl, the luminescence property for blue and violet light of the material quite approaches the blue light chromaticity coordinate (CIE=(0.14, 0.08)) of the International Commission of Illumination (NTSC) the material also has a narrow spectrum full width at half maximum (FWHM); devices prepared by the material can not only effectively reduce device energy consumption, but also adjust the illuminant color of the device through radiation or energy transfer between a subject and an object.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and relates to an electric material, in particular to a fluorinated triphenylamine organic hole transport material and a blue-violet luminescent material. Background technique [0002] Organic electroluminescent devices (OLEDs) have attracted increasing attention due to their wide applications in full-color flat panel displays and solid-state light sources. In particular, triphenylamine materials with simple, multi-branched, and star structures can be used as hole transport materials and electroluminescent materials in organic electroluminescent devices to attract more attention. In OLEDs, maintaining the balance of electron and hole currents is crucial to the performance of the device. However, in most OLEDs, the imbalance of charge transport leads to charge accumulation on the heterostructures, which reduces the efficiency and lifetime of the devices. In add...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/56C07C209/68C09K11/06H01L51/30H01L51/54H01L51/46
CPCY02E10/549
Inventor 吴朝新李战锋焦博侯洵
Owner XI AN JIAOTONG UNIV
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