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Triarylamine compound and organic electroluminescent device thereof

A technology of compound and triarylamine, which is applied in the field of triarylamine compound and its organic electroluminescent device, can solve the problems of material type, thickness and difficulty of matching the refractive index, etc.

Active Publication Date: 2020-10-23
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The light output efficiency of the top-emitting device is theoretically 100%, but due to the plasmonic element effect and waveguide effect of the cathode and the outermost covering layer, there are certain difficulties in matching the material type, thickness, and refractive index. The improvement of performance needs to focus on the selection of cover layer materials, the design of film thickness and structure, and the balance of carrier injection inside the device.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0118] The synthesis of embodiment 1 compound 2

[0119]

[0120] Toluene solvent was added into the reaction flask, followed by 2-(4-bromophenyl)benzoxazole (54.82g, 200mmol), 4-aminobiphenyl (37.23g, 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 20mL of methanol, standing for recrystallization, and filtering to obtain intermediate 2-1 (62.34g, 86%), and the solid purity was detected by HPLC ≧98.9%.

[0121] Add toluene solvent to the reaction flask, and then add intermediate 2...

Embodiment 2

[0123] The synthesis of embodiment 2 compound 22

[0124] In Example 1, the raw material 4-aminobiphenyl is replaced with 4-(benzo[D]oxazol-2-yl)aniline of equimolar amount, and 2-(4-bromophenyl)benzoxazole is replaced with etc. The molar amount of 4-(4-bromophenyl)-dibenzofuran was synthesized according to the synthesis method of compound 2 to obtain compound 22 (59.21 g, 77%), and the solid purity was detected by HPLC ≧99.9%.

[0125] Mass Spectrum m / z: 768.2784 (theoretical value: 768.2777). Theoretical element content (%)C 56 h 36 N 2 o 2 : C, 87.48; H, 4.72; N, 3.64; O, 4.16. Measured element content (%): C, 87.51; H, 4.71; N, 3.63; O, 4.15. 1 H-NMR (500MHz, CDCl3) (δ, ppm): 8.14 (dd, J = 7.5, 1.5Hz, 1H), 8.05 (dd, J = 7.4, 1.5Hz, 1H), 8.00 (d, J = 1.5Hz ,1H),7.92–7.82(m,6H),7.71(s,1H),7.64(dd,J=5.6,3.5Hz,2H),7.60–7.53(m,6H),7.52–7.46(m,5H ), 7.45–7.33(m,8H), 7.29–7.21(m,5H). The above results confirmed that the obtained product was the target product.

Embodiment 3

[0126] The synthesis of embodiment 3 compound 28

[0127] The raw material 4-aminobiphenyl in Example 1 was replaced by an equimolar amount of 4-(benzo[D]oxazol-2-yl)aniline, and compound 28 (57.59g, 80%) was obtained according to the synthesis method of compound 2 , HPLC detection solid purity ≧ 99.9%.

[0128] Mass Spectrum m / z: 791.2586 (Theoretical: 719.2573). Theoretical element content (%)C 51 h 33 N 3 o 2 : C, 85.10; H, 4.62; N, 5.84; O, 4.45. Measured element content (%): C, 85.07; H, 4.63; N, 5.85; O, 4.45. The above results confirmed that the obtained product was the target product.

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Abstract

The invention provides a triarylamine compound and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. According to the invention, a substituted or unsubstituted 9-phenyl-fluorene group and a triarylamine group containing benzoxazole / benzothiazole / benzimidazole / benzotriazole undergoes a reaction to obtain the triarylamine compound by9-position (tertiary C) connection of fluorene. The triarylamine compound has a good hole transport capability, is high in glass transition temperature, good in thermal stability, good in film-forming property, high in refractive index and simple to synthesize, can be applied to an organic electroluminescent device to serve as a hole transport layer and / or a covering layer, can effectively solvethe problems of low luminous efficiency and short service life of the organic electroluminescent device, and has the advantages of high luminous efficiency and long service life.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a triarylamine compound and an organic electroluminescence device. Background technique [0002] Organic electroluminescent device (OLED) is an all-solid-state light-emitting device. In recent years, with the continuous innovation of OLED technology, it has thinner and lighter, wide viewing angle, high brightness, high contrast, high definition, stable image, The advantages of rich colors, fast response, low energy consumption, low temperature, excellent shock resistance, flexibility, and low production cost are increasingly being used in various flat panel display devices, and are considered to be a new type of display that can replace liquid crystal displays. Flat panel display devices have become a hot spot in the research and development of new materials and display technology in recent years. [0003] The excellent performance of organic electroluminesce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/57C07D413/12C07D417/12C07D487/06C07D277/66C07D235/18C07D405/12C07D409/12C07D403/12C07D401/12C07D235/30C07D249/18C07D413/14C07D417/14C07D409/14C07D263/58C07D277/82H01L51/50H01L51/54
CPCC07D263/57C07D413/12C07D417/12C07D487/06C07D277/66C07D235/18C07D405/12C07D409/12C07D403/12C07D401/12C07D235/30C07D249/18C07D413/14C07D417/14C07D409/14C07D263/58C07D277/82H10K85/615H10K85/631H10K85/636H10K85/626H10K85/633H10K85/6576H10K85/657H10K85/6574H10K85/6572H10K30/865H10K50/11
Inventor 朱鸫达王小会
Owner CHANGCHUN HYPERIONS TECH CO LTD
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