Fused ring compound and organic luminescent device thereof
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A technology of organic light-emitting devices and compounds, applied in the field of organic photoelectric materials, to achieve low driving voltage, good electrical and optical properties, and high efficiency
Inactive Publication Date: 2018-01-19
CHANGCHUN HYPERIONS TECH CO LTD
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[0005] At present, the commonly used hole injection layer material is CuPc, and the optimal thickness is 12-18nm. However, wh
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Embodiment 1
[0063]
[0064] Preparation of intermediate A1
[0065] Tri-tert-butylphosphine (4.4 mL of a 1.0M solution in toluene, 1.48 g, 0.05 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium tert-butoxide (22.8 g, 238 mmol) were added to 12-bromo-9H - A solution of dibenzo[a,c]carbazole (63.3 g, 183 mmol) and iodobenzene (38.1 g, 185 mmol) in degassed toluene (1 L), and the mixture was heated at reflux for 2 hours. The reaction mixture was cooled to room temperature, diluted with toluene and filtered through celite. The filtrate was diluted with water and extracted with toluene, and the combined organic phases were evaporated under vacuum. The residue was filtered through silica gel and recrystallized. Intermediate A1 (54.0 g, 70% of theory) was obtained. Mass Spectrum m / z: 422.28 (calculated: 422.32). Theoretical element content (%)C 26 h 16 BrN: C, 73.94; H, 3.82; Br, 18.92; N, 3.32 Measured element content (%): C, 73.95; H, 3.81; Br, 18.92; N, 3.32. The above results ...
Embodiment 2
[0071]
[0072] In Example 1, 2-bromo-9,9-dimethylfluorene was replaced with equimolar 2-bromo-11,11-dimethyl-11H-indeno[b]anthracene, and the other steps were the same to obtain compound 4 . Mass Spectrum m / z: 676.87 (calculated: 676.84). Theoretical element content (%)C 51 h 36 N 2 : C, 90.50; H, 5.36; N, 4.14 Measured element content (%): C, 90.52; H, 5.37; N, 4.11. The above results confirmed that the obtained product was the target product.
Embodiment 3
[0074]
[0075] Compound 11 was obtained by replacing 2-bromo-9,9-dimethylfluorene in Example 1 with equimolar 3-bromo-9,9-diphenylfluorene, and the other steps were the same. Mass Spectrum m / z: 750.99 (calculated: 750.93). Theoretical element content (%)C 57 h 38 N 2 : C, 91.17; H, 5.10; N, 3.73 The measured element content (%): C, 91.15; H, 5.12; N, 3.73. The above results confirmed that the obtained product was the target product.
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Abstract
The invention provides a fused ring compound and an organic luminescent device thereof, and relates to the technical field of an organic photoelectric material. On one hand, the carbazole type structure shows good stability due to relatively high oxidation-reduction potential values; the carbazole type structure is introduced, so that the thermal stability of the fused ring compound is improved. On the other hand, a low-molecular band gap dutrex conjugated unit is introduced, so that the effective conjugated length of the system is expanded; some structures with space torsional strain are used, so that the intermolecular Pi-Pi stacking and the excimer formation are effectively inhabited; the spectrum stability and the glass transition temperature of compounds are improved. On the other hand, fluorene and fluorene derivatives have the characteristics of structure modification simplicity, wide energy gap, high quantum efficiency, high luminescent efficiency, good electrical and optical properties and the like, so that the organic luminescent device prepared by using the fused ring compound provided by the invention shows the advantages of high efficiency and low driving voltage particularly when being used as a hollow injection material in the organic luminescent device, and is superior to the existing common OLED (organic light emitting diode) device.
Description
technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a condensed ring compound and an organic light-emitting device thereof. Background technique [0002] In recent years, organic light-emitting diodes (Organic Light-Emitting Diodes, electroluminescence) rely on their self-illumination, wide viewing angle, fast response speed, vivid color, high definition, high luminous efficiency, low operating voltage, thin panel thickness, and can be manufactured The outstanding advantages of large-size and flexible panels and simple production processes have become a popular emerging flat-panel display industry at home and abroad. [0003] In order to improve the brightness, efficiency and lifetime of organic light emitting devices, multilayer structures are generally used in the devices. These multilayer structures include light-emitting layers and various auxiliary organic layers, such as hole-injection layers, hole-t...
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