Dark blue fluorescent material based on 1,2,4-triazole derivatives and preparation method thereof

A fluorescent material, dark blue technology, applied in the field of non-doped fluorescent materials, can solve the problems of not being able to prepare non-doped fluorescent devices, unable to realize charge transfer excited state, unable to red shift, etc., to improve radiation excitation. effect of electron utilization rate, improving electron transport capability, and high radiation exciton utilization rate

Active Publication Date: 2019-04-23
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since the alkyl chain in this type of material completely breaks the conjugation effect between the donor and acceptor units, the highest occupied molecular orbital (HOMO) and the lowest unoccupied orbital (LUMO) of the molecule are completely localized in the donor and acceptor units. On the bulk unit, the charge transfer from the intramolecular donor to the acceptor cannot be realized, that is, the excited state of the material is only a localized electronic excited state, and the intramolecular charge transfer excited state cannot be realized, making the exciton utilization rate of this type of material Difficult to break through 25%
In addition, since the non-conjugated alkyl chain breaks the conjugation between the donor and the acceptor, the luminescence of the material is located in the ultraviolet region and cannot be red-shifted to the visible region, so it can only be used as a phosphorescent host material and cannot be used For the preparation of non-doped fluorescent devices

Method used

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  • Dark blue fluorescent material based on 1,2,4-triazole derivatives and preparation method thereof
  • Dark blue fluorescent material based on 1,2,4-triazole derivatives and preparation method thereof
  • Dark blue fluorescent material based on 1,2,4-triazole derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 2-cyanopyridine (5.21g, 50mmol), hydrazine hydrate (2.50g, 50mmol), and 25mL of ethanol were sequentially added to a 250mL two-necked round-bottomed flask, and reacted at a low temperature of 0°C for 8 hours to form a viscous light yellow paste. The excess ethanol was removed under vacuum at room temperature, the solid was washed with a small amount of ether, filtered, and dried under vacuum at room temperature for 3 hours to obtain white crystals of (2-pyridine)aminohydrazone.

[0052] Add (2-pyridine)aminohydrazone (4.08g, 30mmol), sodium carbonate (3.15g, 30mmol), 4-bromobenzoyl chloride (7.00g, 30mmol), and 30mL tetrahydrofuran into a 250mL two-necked round-bottomed flask, and react at room temperature for 6h ,filter. The filtrate was dehydrated and ring-closed in 30ml of ethylene glycol at high temperature for 30min, filtered, dried in vacuo for 8h, and recrystallized from ethanol to obtain 2-(3-(4-bromophenyl)-1H-1,2,4-tri Azol-5-yl) pyridine white needle-like cr...

Embodiment 2

[0069] Take 2-(1-phenyl-3-(4-bromophenyl)-1H-1,2,4-triazol-5-yl)pyridine (1.47g, 4mmol) prepared in Example 1, and ( 3-(9H-carbazol-9-yl)phenylboronic acid (1.72g, 6mmol), tetrakis(triphenylphosphine)palladium (90mg, 0.08mmol), sodium carbonate (1.59g, 15mmol), and 100mL tetrahydrofuran were added together In a 250mL two-necked round-bottomed flask, heated to reflux temperature for 24h reaction.Reaction solution was cooled to room temperature, added 50mL water, extracted 3 times with dichloromethane, each dichloromethane consumption 50mL.Merge the organic layers, washed several times, without Dry over magnesium sulfate, filter, distill under reduced pressure, and then purify by petroleum ether / ethyl acetate (2:1) column chromatography to obtain 9-(4'-(1-phenyl-5-(pyridin-2-yl )-1H-1,2,4-triazol-3-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole (TAZ-2Cz) white solid, yield 60% .

[0070] The structural formula of the prepared TAZ-2Cz is as follows.

[0071]

[0072] 1 H NMR (600 ...

Embodiment 3

[0079] Take 2-(1-phenyl-3-(4-bromophenyl)-1H-1,2,4-triazol-5-yl)pyridine (1.88g, 5mmol) prepared in Example 1, and ( 9-Phenyl-9H-carbazol-3-yl)boronic acid (1.72g, 6mmol), tetrakis(triphenylphosphine)palladium (90mg, 0.08mmol), sodium carbonate (1.59g, 15mmol), and 100mL THF together Added to a 250mL two-neck round bottom flask, heated to reflux temperature for 24h. The reaction solution was cooled to room temperature, 50 mL of water was added, and extracted three times with dichloromethane, each time using 50 mL of dichloromethane. The organic layers were combined, washed several times with water, dried over anhydrous magnesium sulfate, filtered, distilled under reduced pressure, and then purified by petroleum ether / ethyl acetate (3:1) column chromatography to obtain 9-phenyl-3-(4-( 1-Phenyl-5-(pyridin-2-yl)-1H-1,2,4-triazol-3-yl)phenyl)-9H-carbazole (TAZ-3Cz) white solid, yield 67 %.

[0080] The structural formula of the prepared TAZ-3Cz is as follows.

[0081]

[00...

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Abstract

The invention discloses a dark blue fluorescent material based on 1,2,4-triazole derivatives represented by general structural formula (I), using 1,2,4-triazole derivatives as acceptor units, Phenylcarbazole or triphenylamine are used as donor units, which are connected through conjugated benzene rings. The structural features of the fluorescent material of the present invention are conducive to the formation of intramolecular charge transfer excited states, increase the utilization rate of radiation excitons, break through the limitation of 25% of the exciton utilization rate of fluorescent materials, and obtain dark blue fluorescent materials. The color coordinate of the OLED device prepared with the fluorescent material of the present invention is smaller than the standard blue light color coordinate.

Description

technical field [0001] The invention relates to a non-doped fluorescent material, in particular to a fluorescent material with a triazole derivative as an acceptor unit and a carbazole derivative as a donor unit. The fluorescent material of the invention can realize deep blue light emission. Background technique [0002] Organic electroluminescent devices (OLED: Organic-light emitting devices) have attracted widespread attention due to their advantages such as high efficiency and fast response. In full-color display and lighting, blue light materials, especially deep blue light materials, are essential. However, compared with green and red light materials, the development of blue light materials is obviously lagging behind, which has seriously restricted the process of OLED industrialization. Although some blue phosphorescent materials based on heavy metals and thermally activated delayed fluorescent materials have been reported in recent years, blue light devices based on...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D401/14C09K11/06H01L51/54
CPCC09K11/06C07D401/04C07D401/14C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1059H10K85/631H10K85/654H10K85/6572
Inventor 许慧侠王科翔李洁孙鹏王芳苗艳勤王华许并社
Owner TAIYUAN UNIV OF TECH
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