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Chrysene compound containing imidazole structure and organic light-emitting device thereof

An organic light-emitting device, imidazole-containing technology, applied in the direction of light-emitting materials, organic chemistry, electric solid devices, etc., can solve the problem that the electronic energy level and the device motor energy level are poorly matched, and it is difficult to take into account the efficiency, stability and color purity, impact. Effective carrier injection and other issues, to achieve the effect of enhancing hole transport capacity, increasing electron transport capacity, and good application effects

Inactive Publication Date: 2018-09-21
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the development of blue-light materials has been relatively slow compared with green-light and red-light materials. This is mainly due to the wide band gap of blue-light organic semiconductor materials, and the poor matching between the electronic energy level and the device’s electrical energy level, which affects the current carrying capacity. The effective injection of particles makes it difficult for this type of material to take into account issues such as efficiency, stability, and color purity.

Method used

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  • Chrysene compound containing imidazole structure and organic light-emitting device thereof
  • Chrysene compound containing imidazole structure and organic light-emitting device thereof
  • Chrysene compound containing imidazole structure and organic light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] [Example 1] Synthesis of Compound A2

[0058]

[0059] Synthesis of compound a

[0060] Add 100mL THF to a three-neck flask containing 6,12-dibromochrysene (16.1g, 42.4mmol), under nitrogen protection, stir at -78°C for 30 minutes, then add 21mL n-butyllithium (2.5M) and react 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 value of the solution 4-5, and the liquid was separated after standing, the aqueous layer was extracted with ethyl acetate, the organic layers were combined, and spin-dried to obtain compound a (11.7g, yield 80%) .

[0061] Synthesis of compound b

[0062] 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 2-bromo-1H - A solution of benzimidaz...

Embodiment 2

[0070] [Example 2] Synthesis of Compound A15

[0071] The bromobenzene in Example 1 was replaced by equimolar 2-bromo-9,9-dimethylfluorene, and the other steps were the same as in Example 1 to obtain the target compound A15. Mass Spectrum m / z: 703.23 (calculated: 703.32). Theoretical element content (%)C 52 h 37 N 3 : C, 88.73; H, 5.30; N, 5.97 The measured element content (%): C, 88.72; H, 5.32; N, 5.96. The above results confirmed that the obtained product was the target product.

Embodiment 3

[0072] [Example 3] Synthesis of Compound A24

[0073] The diphenylamine in Example 1 was replaced by equimolar 9H-carbazole, and the other steps were the same as in Example 1 to obtain the target compound A24. Mass Spectrum m / z: 585.27 (calculated: 585.22). Theoretical element content (%)C 43 h 27 N 3 : C, 88.18; H, 4.65; N, 7.17 Measured element content (%): C, 88.19; H, 4.65; N, 7.16. The above results confirmed that the obtained product was the target product.

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PUM

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Abstract

The invention discloses a chrysene compound containing an imidazole structure and an organic light-emitting device (OLED) thereof and relates to the technical field of organic photoelectric materials.On one hand, a chrysene structure has a relatively high triplet state energy level and a relatively wide energy gap, so that the chrysene structure has blue light performance with excellent performance; on the other hand, the electron transmission capability of the structure is enhanced through connecting benzimidazole, naphthalimidazole, phenanthridazole or pyridine imidazole groups in a molecule, the hole transport capability of the structure is enhanced through connecting triarylamine, carbazole and acridine structures in the molecule; the enhanced electron transmission capability and enhanced hole transport capability are combined so that the transmission of a current carrier is balanced. The chrysene compound is applied to the organic light-emitting device and is especially used as ablue doping material in a light-emitting layer; the device has the advantages of low driving voltage and high light-emitting efficiency, and is better than an existing commonly-used OLED (organic light emitting diode) device. The chrysene compound has a good application effect in the OLED devices so that the chrysene compound has a good industrialized prospect.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a chrysene compound containing an imidazole 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] A general organic light-emitting device (OLED) is composed of a cathode, an anode, and an organic layer inserted between the cathode a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C07D403/10C07D401/10C07D413/10C07D401/14C07D403/14C07D405/14C07D409/14C07D235/02C07D405/04C07D403/04C07D409/12C07D405/12C07D403/12C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D235/02C07D235/18C07D401/10C07D401/14C07D403/04C07D403/10C07D403/12C07D403/14C07D405/04C07D405/12C07D405/14C07D409/12C07D409/14C07D413/10C09K2211/1011C09K2211/1007C09K2211/1029C09K2211/1037C09K2211/1033C09K2211/1044C09K2211/1059C09K2211/1092C09K2211/1088H10K85/622H10K85/626H10K85/654H10K85/6576H10K85/657H10K85/6572H10K85/6574H10K50/11
Inventor 刘喜庆蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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