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Arylamine compound containing fluorene groups and organic light-emitting device thereof

A technology of organic light-emitting devices and compounds, applied in the field of organic photoelectric materials, can solve the problems of device efficiency and lifespan degradation, damage to film uniformity, damage to interface contact, etc., and achieve low driving voltage, good industrialization prospects, and high luminous efficiency. Effect

Inactive Publication Date: 2018-10-23
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Crystallization will destroy the uniformity of the film, and at the same time destroy the good interfacial contact between the hole transport layer, the anode and the organic layer, resulting in a decrease in the efficiency and life of the device.

Method used

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  • Arylamine compound containing fluorene groups and organic light-emitting device thereof
  • Arylamine compound containing fluorene groups and organic light-emitting device thereof
  • Arylamine compound containing fluorene groups and organic light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] [Example 1] Synthesis of Compound 1-6

[0076]

[0077] Synthesis of intermediate a1-6

[0078]Tri-tert-butylphosphine (4.4 mL of a 1.0 M 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 N,N'- A solution of diphenylbenzidine (61.5 g, 183 mmol) and 3-bromo-9,9-dimethylfluorene (49.9 g, 183 mmol) in degassed toluene (1 L), and the mixture was heated at reflux for 2 Hour. 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 a1-6 (77.3 g, 80% yield) was obtained.

[0079] Mass Spectrum m / z: 528.63 (calculated: 528.68). Theoretical element content (%)C 39 h 32 N 2 : C, 88.60; H, 6.10; N, 5.30 The measured element content (%): C, ...

Embodiment 2

[0092] [Example 2] Synthesis of Compound 1-17

[0093]

[0094] Replace N,N'-diphenylbenzidine in Example 1 with equimolar N,N'-diphenylbenzidinediamine, and 3-bromo-9,9-dimethylfluorene with equimolar 2-bromo-dibenzofuran, other steps are the same as the synthesis of Example 1 to obtain the target product compound 1-17. Mass Spectrum m / z: 816.93 (calculated: 816.98). Theoretical element content (%)C 61 h 40 N 2 O: C, 89.68; H, 4.93; N, 3.43; O, 1.96 Measured element content (%): C, 89.67; H, 4.94; N, 3.41; O, 1.98. The above results confirmed that the obtained product was the target product.

Embodiment 3

[0095] [Example 3] Synthesis of Compound 1-38

[0096]

[0097] The N,N'-diphenylbenzidine in Example 1 was replaced by an equimolar compound A, and the other steps were the same as in Example 1 to obtain the target compound 1-38. Mass Spectrum m / z: 883.26 (calculated: 883.13). Theoretical element content (%)C 67 h 50 N 2 : C, 91.12; H, 5.71; N, 3.17 Measured element content (%): C, 91.13; H, 5.72; N, 3.15. The above results confirmed that the obtained product was the target product.

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Abstract

The invention discloses an arylamine compound containing fluorene groups and an organic light-emitting device thereof and relates to the technical field of organic photoelectric materials. The arylamine compound disclosed by the invention has the beneficial effects that the fluorene groups are three-dimensional space structure, so that the intermolecular aggregation can be effectively prevented and the crystallization is not easy; due to the advantages of easy modification and strong rigidity in the fluorene groups, the compound is stable in structure, and especially for indenofluorene groups,the rigid characteristic of the fluorene groups is improved, the stability of the compound containing the structure is greatly improved and the molecular weight of the compound is increased, so thatthe vitrification temperature is high; after the arylamine compound is applied to the organic light-emitting devices as a cavity transmission layer, the device shows the advantages of low driving voltage and high light-emitting efficiency, and is superior to the existing common OLED (Organic Light Emitting Diode) devices; the arylamine compound shows good application effect in the OLED light-emitting devices, so that the industrial prospect is good.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine compound containing a fluorene group 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] As the hole transport layer in OLED, its basic function is to improve the transport efficiency of holes in the device, effectively bl...

Claims

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Application Information

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IPC IPC(8): C07C211/54C07C211/61C07C211/58C07D307/91C07D333/76C07D209/88C07D209/94C07D219/08C07D209/86C07D405/12C07D409/12C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07C211/54C07C211/58C07C211/61C07D209/86C07D209/88C07D209/94C07D219/08C07D307/91C07D333/76C07D405/12C07D409/12C07C2603/18C07C2603/24C07C2603/52C07C2603/40C07C2603/54C09K2211/1092C09K2211/1088C09K2211/1029C09K2211/1014C09K2211/1011C09K2211/1007H10K85/623H10K85/622H10K85/615H10K85/631H10K85/636H10K85/626H10K85/633H10K85/6576H10K85/6572H10K85/6574H10K50/11H10K50/15
Inventor 刘喜庆蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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