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Triazine compound containing fluorine structure, and organic light-emitting devices thereof

A technology of organic light-emitting devices and triazine compounds, which is applied in the field of organic photoelectric materials, can solve problems such as device performance degradation, and achieve the effects of low driving voltage, high luminous efficiency, and cost savings

Inactive Publication Date: 2019-01-22
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The hole mobility of the hole transport material in the device is generally much greater than the electron mobility of the electron transport material, which will cause a significant decrease in device performance

Method used

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  • Triazine compound containing fluorine structure, and organic light-emitting devices thereof
  • Triazine compound containing fluorine structure, and organic light-emitting devices thereof
  • Triazine compound containing fluorine structure, and organic light-emitting devices thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] [Example 1] Synthesis of Compound A1

[0058]

[0059] Synthesis of intermediate a1-1

[0060] Take 2-(3,5-dichlorophenyl)pyridine (9.5g, 42.4mmol) into a three-necked flask, add THF 100mL, protect with nitrogen, stir at -78°C for 30 minutes, then add n-butyllithium (2.5M) 21 mL, reacted for 1 hour, then added 14 g of triisopropyl borate, reacted at low temperature for 1 hour, and gradually returned to room temperature. In the post-treatment process, 2M hydrochloric acid was added to the system to make the pH of the solution 4-5, and the liquid separation was allowed to stand. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, and spin-dried to obtain intermediate a1-1 (8.2g, yield 80%).

[0061] Mass Spectrum m / z: 242.86 (calculated: 242.83). Theoretical element content (%)C 11 h 11 B 2 NO 4 : C, 54.41; H, 4.57; B, 8.90; N, 5.77; O, 26.35 The measured element content (%): C, 54.41; The above results confirmed that the obtai...

Embodiment 2

[0068] [Example 2] Synthesis of Compound A13

[0069]

[0070] The 2-bromo-9,9-dimethylfluorene in Example 1 was replaced by equimolar 2-bromo-9,9-spirobifluorene, and the other steps were the same as the synthesis of Example 1 to obtain the target product compound A13. Mass Spectrum m / z: 1092.26 (calculated: 1092.29). Theoretical element content (%)C 81 h 49 N 5 : C, 89.07; H, 4.52; N, 6.41 Measured element content (%): C, 89.08; H, 4.51; N, 6.41. The above results confirmed that the obtained product was the target product.

Embodiment 3

[0071] [Example 3] Synthesis of Compound A27

[0072]

[0073] In Example 1, the 2-bromo-9,9-dimethylfluorene was replaced by equimolar 2-bromo-9,9-diphenylfluorene, and 2-(3,5-dichlorobenzene)pyridine was replaced by Equimolar 3-(3,5-dichlorophenyl)pyridine, and other steps were the same as in Example 1 to obtain the target compound A27. Mass Spectrum m / z: 1096.26 (calculated: 1096.32). Theoretical element content (%)C 81 h 53 N 5: C, 88.74; H, 4.87; N, 6.39 Measured element content (%): C, 88.76; H, 4.86; N, 6.38. The above results confirmed that the obtained product was the target product.

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Abstract

The invention discloses a triazine compound containing a fluorine structure, and organic light-emitting devices thereof, and belongs to the technical field of organic photoelectric material. On one hand, triazine group is a typical strong electrondrawing group, so that the compounds taking triazine groups as center structures are high in electron mobility and low in energy level; connection with pyridine groups is adopted, the compound electron mobility is increased obviously; on the other hand, the triazine group is of a three dimensional structure, is capable of preventing intermolecular aggregation effectively, and inhibiting crystallization; the easy modification performance and the high rigidity of triazine groups are capable of stabilizing compound structures; and at last, the compound structure contains an extensible three dimensional structure, the continuous pi conjugated system is capable of achieving relatively electron fluidity, so that the electron mobility is relatively high; combination of the above advantages is capable of realizing transmission balance of charge carriers. The triazine compound containing a fluorine structure is applied in the organic light-emittingdevices as electron transmission layers or cavity barrier layers, so that the organic light-emitting devices are low in driving voltage and high in light emitting efficiency.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a triazine compound containing a fluorene structure and an organic light-emitting device thereof. Background technique [0002] Organic light emitting diode (Organic Light Emitting Diode, OLED) is a light-emitting device prepared by using electrons and holes to recombine light in organic thin films. High, with high contrast, pure color, almost no problem of viewing angle; (3) ultra-thin, composed of very thin organic material coating and matrix material, small in size and suitable for portable products; (4) power consumption Very small, environmentally friendly and energy-saving; (5) fast response speed, one thousandth of that of LCD; (6) wide operating temperature range, and can still display normally at -40°C. [0003] Organic charge transport materials are a class of organic semiconductor materials that can achieve controllable directional and ordered ...

Claims

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Application Information

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IPC IPC(8): C07D401/10C07D401/14C07D405/14C07D409/14C09K11/06H01L51/54
CPCC09K11/06C07D401/10C07D401/14C07D405/14C07D409/14C09K2211/1011C09K2211/1088C09K2211/1092C09K2211/1059H10K85/624H10K85/615H10K85/626H10K85/654H10K85/6576H10K85/6574H10K85/6572
Inventor 刘喜庆蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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