Triamine derivative and organic electroluminescent device thereof

An amine derivative and electroluminescence technology, which is applied in the fields of electric solid devices, electrical components, organic chemistry, etc., can solve the problems of blocking electrons and low luminous efficiency of organic electroluminescence devices, and achieve the effect of improving luminous efficiency.

Active Publication Date: 2020-05-29
CHANGCHUN HYPERIONS TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the problems that the current hole transport materials cannot effectively block electrons, the light extraction materials cannot effectively couple the light trapped in the device, and the luminous efficiency of organic electroluminescent devices is low, the invention provides a triamine Derivatives and their organic electroluminescent devices

Method used

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  • Triamine derivative and organic electroluminescent device thereof
  • Triamine derivative and organic electroluminescent device thereof
  • Triamine derivative and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0102] Compound preparation

[0103] Description of raw materials and reagents: The raw materials and reagents used in the present invention are reagent pure.

[0104]Description of characterization equipment: mass spectrometry uses AXIMA-CFRplus matrix-assisted laser desorption ionization flight mass spectrometer from Kratos Analytical Company of Shimadzu Group, and chloroform is used as solvent. For elemental analysis, a Vario EL cube organic elemental analyzer from German Elementar Company was used, and the sample mass was 5-10 mg. NMR ( 1 HNMR) use Bruker-510 nuclear magnetic resonance spectrometer (Germany Bruker company), 600MHz, CDCl 3 as solvent and TMS as internal standard.

Synthetic example 1

[0105] Synthesis Example 1: Preparation of Compound 1

[0106]

[0107] (1) Under nitrogen protection, add sodium tert-butoxide (28.8g, 0.30mol), bis(4-bromophenyl)amine (32.7g, 0.10mol), 2-(4-bromobenzene) to a 500ml reaction flask Base) benzoxazole (27.4g, 0.10mol), tris(dibenzylideneacetone) dipalladium (91.5mg, 0.10mmol), toluene (250ml), stirred for 30 minutes, added tri-tert-butylphosphine (0.10mL 1.0 M toluene solution, 0.10 mmol), reacted under reflux conditions for 13 hours. Pour the reaction solution into a 1.5 liter beaker, add toluene (200ml) and water (400ml), stir for 10 minutes, filter with suction, rinse the filter cake with water until the filtrate is neutral, then rinse with toluene and ethanol respectively, and Dry and recrystallize with ethanol to obtain solid intermediate A-1 (42.1 g, yield 81%), and the solid purity is ≧99.9% as detected by HPLC.

[0108] (2) Under nitrogen protection, add 4-(2-benzoxazolyl)aniline (47.3g, 0.225mol), bromobenzene (23...

Synthetic example 2

[0110] Synthesis Example 2: Preparation of Compound 6

[0111]

[0112] The bromobenzene in Synthetic Example 1-(2) was replaced by equimolar 9,9-dimethyl-2-bromofluorene, and the other steps were the same to obtain compound 6 (52.4g, the yield was about 75%), HPLC Detect solid purity ≧99.9%. Mass Spectrum m / z: 1162.23 (calculated: 1163.39). Theoretical element content (%)C 81 h 58 N 6 o 3 : C, 83.63; H, 5.03; N, 7.22; O, 4.13; Measured element content (%): C, 83.12; H, 5.11; N, 7.14; O, 4.25. The above results confirmed that the obtained product was the target product.

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Abstract

The invention discloses a triamine derivative and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. The technical problems to be solved in the invention are that a current hole transport material cannot effectively block electrons, a light extraction material cannot effectively couple out light trapped in a device, and the light emitting efficiency of an organic electroluminescent device is low. The triamine derivative disclosed by the invention at least contains one benzoxazolyl group or benzothiazolyl group. The organic electroluminescent device comprises an anode, a light-emitting layer and a cathode and further comprises a hole transport layer or a light extraction layer, and the triamine derivative is contained in thehole transport layer or the light extraction layer. The triamine derivative disclosed by the invention can be used as a hole transport material and a light extraction material, and can effectively improve the light-emitting efficiency of the device when being applied to the organic electroluminescent device.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a triamine derivative and an organic electroluminescence device thereof. Background technique [0002] An organic light-emitting diode (Organic Light-Emitting Diode, OLED) is also called an organic light-emitting device (Organic Light-Emitting Device, OLED). Organic electroluminescent devices are devices that use organic materials as active light-emitting layers under the action of an electric field. Since Deng Qingyun and Van Slyke successfully prepared the first low-voltage-driven organic electroluminescent device in 1987, OLED has received extensive attention and has achieved rapid development. According to its inherent characteristics and advantages, It has good industrialization prospects mainly in flat panel display and solid state lighting. Compared with the traditional liquid crystal display (LCD), OLED has many advantages such as wide viewing an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/57C07D413/14C07D417/14H01L51/50H01L51/52H01L51/54
CPCC07D263/57C07D413/14C07D417/14H10K85/624H10K85/622H10K85/631H10K85/6576H10K85/6574H10K85/657H10K50/156H10K50/18H10K50/15H10K50/85
Inventor 孙敬朱鸫达鲁秋
Owner CHANGCHUN HYPERIONS TECH CO LTD
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