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Aromatic amine compound and organic electroluminescent devices thereof

A compound and aromatic amine technology, applied in the field of organic electroluminescence, can solve the problems of inability to effectively block exciton luminescence efficiency, low light extraction efficiency of the cover layer, low glass transition temperature, etc., achieve good hole transport ability, and improve recombination rate. and the effect of high utilization rate and high refractive index

Active Publication Date: 2020-02-28
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to solve the poor thermal stability caused by the low glass transition temperature of hole transport materials at the present stage, the low luminous efficiency caused by the inability to effectively block the escape of excitons to the anode side, and the low light extraction efficiency caused by the low refractive index of the covering layer, the present invention An aromatic amine compound and an organic electroluminescent device thereof are provided. The aromatic amine compound provided by the present invention has good hole transport ability, high glass transition temperature, high triplet energy level, thermal stability, The film-forming property is good, the refractive index is high, and the synthesis is simple. The organic electroluminescent device provided by the present invention containing the aromatic amine compound of the present invention has the advantages of good thermal stability, high luminous efficiency and long service life.

Method used

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  • Aromatic amine compound and organic electroluminescent devices thereof
  • Aromatic amine compound and organic electroluminescent devices thereof
  • Aromatic amine compound and organic electroluminescent devices thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] The synthesis of embodiment 1 compound 2

[0118]

[0119]Toluene solvent was added into the reaction flask, followed by 3-bromo-N-phenylcarbazole (33.85g, 200mmol), 4-aminobiphenyl (70.89g, 220mmol), sodium tert-butoxide (57.66g, 600mmol), After vacuuming and replacing with nitrogen for three times, add Pd(OAc) 2 (0.9g, 4.0mmol), after vacuumizing and nitrogen replacement three times, add P(t-Bu) 3 (6.4mL of 1.0M toluene solution, 6.4mmol), and nitrogen replacement was performed three times, and the mixture was refluxed for 2h under nitrogen atmosphere. After the reaction was stopped, the mixture was cooled to room temperature, filtered through diatomaceous earth to obtain the filtrate, and the filtrate was concentrated , adding 20 mL of methanol, standing for recrystallization, and filtering to obtain compound 2-1 (68.97 g, 84%), and the purity of the solid was detected by HPLC ≧99.9%.

[0120] Add 500mL of THF and raw material a-1 (35.01g, 200mmol) into the reac...

Embodiment 2

[0124] The synthesis of embodiment 2 compound 26

[0125] The raw material 4-aminobiphenyl in Example 1 was replaced with an equimolar amount of 2-amino-9,9-spirobifluorene, and compound 26 (51.76 g, 79%) was obtained according to the synthesis method of compound 2, and the purity of the solid was detected by HPLC ≧99.9%.

[0126] Mass Spectrum m / z: 818.43 (calculated: 818.37). Theoretical element content (%)C 62 h 46 N 2 : C, 90.92; H, 5.66; N, 3.42. Measured element content (%): C, 90.95; H, 5.65; N, 3.40. 1 H-NMR (500MHz, CDCl 3 )(δ,ppm): 8.39(dd,J=7.4,1.5Hz,1H),8.08(dd,J=7.4,1.5Hz,1H),7.95–7.86(m,3H),7.82(dd,J= 6.9,5.1Hz,3H),7.78(d,J=1.5Hz,1H),7.69–7.64(m,2H),7.64–7.55(m,J=7.3,5.7Hz,7H),7.55–7.51(m ,2H),7.49(d,J=1.6Hz,2H),7.46–7.41(m,4H),7.41–7.35(m,6H),7.35–7.31(m,J=7.5,1.5Hz,1H), 7.31–7.26(m, J=7.5, 2.1Hz, 1H), 7.12(dd, J=7.5, 1.4Hz, 1H), 2.65(q, J=7.1Hz, 1H), 2.32(d, J=4.8Hz , 2H), 1.86–1.79 (m, J=13.6, 7.0Hz, 1H), 1.63 (d, J=7.3Hz, 4H), 1.46–1.36 (m, 1H), 1.3...

Embodiment 3

[0127] The synthesis of embodiment 3 compound 67

[0128] The raw material 4-aminobiphenyl in Example 1 was replaced with an equimolar amount of 3-aminodibenzofuran, and compound 67 (42.94 g, 80%) was obtained according to the synthesis method of compound 2, and the solid purity was detected by HPLC ≧99.9%.

[0129] Mass Spectrum m / z: 670.38 (calculated: 670.30). Theoretical element content (%)C 49 h 38 N 2 O: C, 87.73; H, 5.71; N, 4.18; O, 2.38. Measured element content (%): C, 87.75; H, 5.70; N, 4.18; O, 2.37. The above results confirmed that the obtained product was the target product.

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Abstract

The invention provides an aromatic amine compound and organic electroluminescent devices thereof, and relates to the technical field of organic photoelectric materials. According to the invention, a specific heteroaryl group and a bicyclic heptane group are introduced into a triarylamine structure to obtain the aromatic amine compound disclosed by the invention; the aromatic amine compound has good hole transport capability, high glass transition temperature, excellent thermal stability, excellent film-forming property, high refractive index and simple synthesis process, can be applied to theorganic electroluminescent devices as a hole transport layer and / or a covering layer, can effectively solve the problems of poor thermal stability, low luminous efficiency and short service life of the organic electroluminescent devices; and the advantages of high luminous efficiency and long service life of the organic electroluminescent devices are achieved.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to an aromatic amine compound and an organic electroluminescence device. Background technique [0002] With the advent of the information age, research on new types of displays for man-machine interfaces has attracted more and more attention, especially the technology of various flat panel display devices. Wide, high-definition, image stability, rich colors, fast response, low energy consumption, low temperature, excellent shock resistance, flexibility, and low production costs are increasingly being used in mobile phones, personal electronic assistants (PDAs), digital Cameras, vehicle displays, notebook computers, televisions, and military fields are considered to be a new type of flat panel display device that can replace liquid crystal displays. research and development hotspots. [0003] The original organic electroluminescent device can be realized by spin...

Claims

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Application Information

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IPC IPC(8): C07D209/88C07D405/12C07D409/12C07D401/12C07D471/10C07D487/06C07D471/04C07D417/12C07D413/12C07D411/12C07D307/91C07D407/12C07D333/76C07D265/38C07D219/08C07D311/82C07D209/80C07D307/77C07D327/08C07D279/22C07D311/96H01L51/50H01L51/54
CPCC07D209/88C07D405/12C07D409/12C07D401/12C07D471/10C07D487/06C07D471/04C07D417/12C07D413/12C07D411/12C07D307/91C07D407/12C07D333/76C07D265/38C07D219/08C07D311/82C07D209/80C07D307/77C07D327/08C07D279/22C07D311/96H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/15
Inventor 董秀芹王英雪鲁秋
Owner CHANGCHUN HYPERIONS TECH CO LTD
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