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Heterocyclic compound and organic electroluminescent device thereof

A heterocyclic compound and electroluminescence technology, which is applied in the materials of organic semiconductor devices, electric solid devices, organic chemistry, etc., can solve the problem that the refractive index is only about 1.90, and can increase the glass transition temperature and improve the transmittance. , The effect of improving the light output efficiency

Active Publication Date: 2019-11-22
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The Japanese patent with the publication number JP2017123341 discloses a covering layer material of arylamine derivatives, which improves the light extraction efficiency to a certain extent, but the refractive index of the material is only about 1.90

Method used

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  • Heterocyclic compound and organic electroluminescent device thereof
  • Heterocyclic compound and organic electroluminescent device thereof
  • Heterocyclic compound and organic electroluminescent device thereof

Examples

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preparation example Construction

[0066] The preparation method of the heterocyclic compound of the present invention can be prepared by a conventional coupling reaction, for example, it can be prepared by the following synthetic route, but the present invention is not limited thereto:

[0067]

[0068] Compound (a) reacts with compound (b) by Suzuki to obtain intermediate (A), or compound (a) reacts with compound (c) by Suzuki to obtain intermediate (B), or compound (d) and compound (e ) through the Buchwald reaction to obtain the intermediate (C); the intermediate (A), (B) or (C) reacts with the halide (f) Br-L-Br or I-L-Br containing the L group again, Finally, the target compound shown in formula (I) is obtained.

[0069] Among them, the L, L 1 , X, R 1 The definitions of , m, and n are as described above, and will not be repeated here.

[0070] In the present invention, there is no special limitation on the reaction conditions of the above reactions, and the reaction conditions well known to those s...

Embodiment 1

[0105] Embodiment 1: the preparation of compound 9

[0106]

[0107] Under nitrogen protection, compound a-1 (4.89g, 30mmol), compound b-1 (7.46g, 30.3mmol), K 2 CO 3 (12.44g, 90mmol), stirred with 300mL of toluene solvent. Add catalyst Pd(PPh 3 ) 4 (0.35g, 0.3mmol), 50mL of distilled water, the temperature was raised to reflux, and the reaction was stirred for 10h. After fully reacting, 75 mL of distilled water was added to terminate the reaction. The crude intermediate A-1 was obtained by filtration under reduced pressure, washed three times with distilled water, and then recrystallized with toluene and ethanol (10:1) to obtain 6.65 g of the target compound A-1 with a yield of 78%.

[0108] Under argon atmosphere, dissolve intermediate A-1 (5.74g, 20.2mmol), f-1 (3.12g, 10mmol), sodium tert-butoxide (2.40g, 25mmol) in 100ml dehydrated toluene, and add palladium acetate under stirring (0.04g, 0.2mmol), a toluene solution of tri-tert-butylphosphine (0.16g, 0.8mmol), a...

Embodiment 2

[0110] Embodiment 2: the preparation of compound 12

[0111]

[0112] Bromide b-1 was replaced by bromide b-2 in an equimolar amount, and other steps were the same as in Example 1 to obtain compound 12. Mass Spectrum m / z: 818.39 (calculated: 818.27). Theoretical element content (%)C 58 h 34 N 4 o 2 : C, 85.07; H, 4.18; N, 6.84; O, 3.91. Measured element content (%): C, 85.14; H, 4.21; N, 6.89; O, 3.90. The above results confirmed that the obtained product was the target product.

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Abstract

The invention provides a heterocyclic compound and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials. The heterocyclic compound provided by the invention has a high refractive index, the refractive index can reach 1.95-2.10, and when the heterocyclic compound is used as a covering layer material, the transmittance of a semi-transmissiveelectrode can be improved, the light emitting direction can be adjusted, and the light emitting efficiency can be improved. Secondly, according to the heterocyclic compound provided by the invention,by optimizing the structure and introducing nitrogen-containing five-membered heterocycle or six-membered heterocycle, benzoxazole or benzothiazole groups, the glass-transition temperature is increased, the film-forming property and stability are better, and the service lifetime of the device can be effectively prolonged when the heterocyclic compound is used as a covering layer material of the organic light-emitting device.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a heterocyclic compound and an organic electroluminescence device thereof. Background technique [0002] Organic Light-Emitting Diode (OLED) is an all-solid-state light-emitting device with high brightness, high contrast, high definition, wide viewing angle, wide color gamut, ultra-thin, ultra-light, low power consumption, wide Temperature, self-illumination, high luminous efficiency, short response time, transparency, flexibility, etc., have been commercialized in the fields of mobile phones, TVs, and micro-displays. Potential new display technology. [0003] Since total reflection occurs at the interface between the ITO thin film of the organic light-emitting diode and the glass substrate or the interface between the glass substrate and the air, only 20% of the emitted light can be used, and the remaining 80% of the light is limited to conversion inside...

Claims

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Application Information

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IPC IPC(8): C07D413/14C07D417/14H01L51/50H01L51/54
CPCC07D413/14C07D417/14H10K85/623H10K85/624H10K85/622H10K85/615H10K85/631H10K85/633H10K85/657H10K85/6572H10K85/656H10K85/636H10K50/8445H10K2102/00
Inventor 杜明珠刘辉赵倩王小会
Owner CHANGCHUN HYPERIONS TECH CO LTD
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