Bipyridine fluorene derivatives, preparation method and application thereof, and electroluminescent device

An electroluminescent device and a technology of dipyridine fluorenes are applied in the field of preparation of dipyridine fluorene derivatives, electroluminescent devices, and can solve the problem of low triplet energy level, weak electron transport ability, and inability to satisfy blue light phosphorescence. devices, etc., to achieve the effect of increasing the glass transition temperature, enhancing the triplet energy level, and being conducive to the development of high-efficiency full-color displays

Active Publication Date: 2014-01-15
TCL CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the fact that the fluorenyl unit is composed of two benzene rings, the electron transport ability of the existing fluorene-based phosphorescent host materials is relatively weak. At the same time, due to the conjugated structure of the fluorene-based unit, the existing triplet energy level Relatively low, therefore, the existing fluorene-based phosphorescent host materials cannot meet the requirements of blue phosphorescent light-emitting devices

Method used

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  • Bipyridine fluorene derivatives, preparation method and application thereof, and electroluminescent device
  • Bipyridine fluorene derivatives, preparation method and application thereof, and electroluminescent device
  • Bipyridine fluorene derivatives, preparation method and application thereof, and electroluminescent device

Examples

Experimental program
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Effect test

Embodiment 1

[0057] Preparation of 9-phenyl-9-(4,4-dimethyltriphenylamino)-4,5-dipyridinefluorene (MTAPF):

[0058] 9-Phenyl-9-hydroxy-4,5-dipyridinefluorene (1.0 mmol), 4,4′-dimethyltriphenylamine (1.2 mmol) were dissolved in dry dichloromethane (20 ml), while Add trifluoromethane acid (1.0 mmol) under nitrogen atmosphere, heat to 110°C and reflux for 24 hours in the dark. Then cool to room temperature, add water to quench the reaction, extract with dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, filter, remove the organic solvent, and recrystallize with dichloromethane and methanol to obtain white solid powder 9-phenyl-9- (4,4-Dimethyltriphenylamino)-4,5-dipyridinefluorene (MTAPF). Yield: 59%. Mass Spectrum (Mass Spectrum) MS (APCI): calcd for C37H29N3: 515.2, found, 516.4 (M+1)+.

Embodiment 2

[0060] Preparation of 4-methyl-4′,4″-bis(9-phenyl-4,5-diaza-9-fluorenyl)triphenylamine (TADPF):

[0061] Using a method similar to the compound MTAPF, the difference is that 4-methyltriphenylamine is used instead of 4,4'-dimethyltriphenylamine as the starting material, and the ratio of raw materials is changed, 9-phenyl-9-hydroxyl- The molar mass ratio of 4,5-dipyridine fluorene to 4-methyltriphenylamine and trifluoromethane acid is 2.5: 1: 2.5. 4-Methyl-4′,4″-bis(9-phenyl-4,5-diaza-9-fluorenyl)triphenylamine (TADPF) white solid powder can be obtained, yield: 64%. Mass spectrum MS (APCI): calcd for C53H37N5: 743.3, found, 744.4 (M+1)+.

Embodiment 3

[0063] Preparation of 9,9-bis(4,4′-dimethyltriphenylamino)dipyridylfluorene (DTAPF):

[0064] Using a method similar to the compound MTAPF, the difference is that 9-phenyl-9-hydroxyl-4,5-dipyridine fluorene is used as the starting material instead of 9-phenyl-9-hydroxy-4,5-dipyridine fluorene, and 4,4′-bispyridine fluorenone is combined with 4,4′-dipyridine The molar mass ratio of methyltriphenylamine and trifluoromethane is: 1: 2.5: 2. 9,9-bis(4,4′-dimethyltriphenylamino)dipyridylfluorene (DTAPF) white solid powder can be obtained, yield: 90%. Mass MS (APCI): calcd for C51H42N4: 710.3, found, 711.3 (M+1)+.

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Abstract

The invention discloses bipyridine fluorene derivatives, a preparation method and application thereof, and an electroluminescent device. The molecular structure general formula of the bipyridine fluorene derivatives is shown as a figure in the specification. According to the bipyridine fluorene derivatives, bipyridine fluorene with special electron transmission performance is connected with a triphenylamine group with high hole transmission speed on the 9-position of fluorene; due to strong steric hindrance of the 9-position of fluorene, a more distorted molecular structure is realized, the triple state energy level of a host compound is enhanced, and the glass transition temperature of the host compound is increased. The bipyridine fluorene derivatives are used for preparing a high-efficiency electroluminescent device, so stability of the device is promoted, the device can achieve excellent electroluminescent performance, and development of a high-efficiency full-color display is promoted.

Description

technical field [0001] The invention relates to the field of organic luminescent materials, in particular to a bipyridine fluorene derivative, a preparation method and application thereof, and an electroluminescent device. Background technique [0002] The fluorenyl unit has more substitution sites, and its chemical structural formula is as follows figure 1 As shown, a variety of compound molecules can be formed, and are widely used in the preparation of organic small molecule materials and polymer molecular materials. Existing fluorene-based phosphorescent host materials have a relatively wide energy band width, and can be well applied as organic small molecules and polymer blue-light fluorescent materials. However, due to the fact that the fluorenyl unit is composed of two benzene rings, the electron transport ability of the existing fluorene-based phosphorescent host materials is relatively weak. At the same time, due to the conjugated structure of the fluorene-based uni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D471/04C07D519/00C09K2211/1029H10K85/636H10K85/6572
Inventor 黄宏付东申智渊邵诗强施建华
Owner TCL CORPORATION
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