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Organic compound containing 9,9'-spirobifluorene as core and OLED (organic light emitting diode) device

A technology of electroluminescent devices and organic compounds, applied in the fields of organic chemistry, electro-solid devices, electrical components, etc., can solve different problems, improve current efficiency and life, improve exciton utilization and high fluorescence radiation efficiency, The effect of good industrialization prospects

Inactive Publication Date: 2018-04-03
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Organic compound containing 9,9'-spirobifluorene as core and OLED (organic light emitting diode) device
  • Organic compound containing 9,9'-spirobifluorene as core and OLED (organic light emitting diode) device
  • Organic compound containing 9,9'-spirobifluorene as core and OLED (organic light emitting diode) device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0137] Embodiment 1: the synthesis of compound 5:

[0138] synthetic route:

[0139]

[0140] In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol 3-bromo-9,9'-spirobifluorene, 0.012mol intermediate A1, 150ml toluene and stir to mix, then add 0.02mol sodium carbonate, 1×10 -4 mol Pd(PPh 3 ) 4 , heated to 105 ° C, reflux reaction for 24 hours, sampling point plate, showing no bromide remaining, the reaction is complete; naturally cooled to room temperature, filtered, the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85 ° C), passed through neutral silica gel Column, obtain target product, HPLC purity 99.1%, yield 72.4%;

[0141] Elemental analysis structure (molecular formula C 52 h 35 NO): Theoretical C, 90.54; H, 5.11; N, 2.03; O, 2.32; Tested: C, 90.53; H, 5.12; N, 2.04;

[0142] HPLC-MS: The molecular weight of the material is 689.27, and the measured molecular weight is 689.53.

Embodiment 2

[0143] Embodiment 2: the synthesis of compound 6:

[0144] synthetic route:

[0145]

[0146] In a 250ml three-neck flask, under nitrogen protection, add 0.01mol 3-bromo-9,9'-spirobifluorene, 0.012mol intermediate B1, 150ml toluene and stir to mix, then add 0.02mol sodium carbonate, 1×10 -4 mol Pd(PPh 3 ) 4 , heated to 105 ° C, reflux reaction for 24 hours, sampling point plate, showing no bromide remaining, the reaction is complete; naturally cooled to room temperature, filtered, the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85 ° C), passed through neutral silica gel Column, obtain target product, HPLC purity 99.2%, yield 71.8%;

[0147] Elemental analysis structure (molecular formula C 52 h 35 NO): Theoretical C, 90.54; H, 5.11; N, 2.03; O, 2.32; Tested: C, 90.55; H, 5.10; N, 2.02;

[0148] HPLC-MS: The molecular weight of the material is 689.27, and the measured molecular weight is 689.57.

Embodiment 3

[0149] Embodiment 3: the synthesis of compound 10:

[0150] synthetic route:

[0151]

[0152] In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol 3-bromo-9,9'-spirobifluorene, 0.012mol intermediate C1, 150ml toluene and stir to mix, then add 0.02mol sodium carbonate, 1×10 -4 mol Pd(PPh 3 ) 4 , heated to 105 ° C, reflux reaction for 24 hours, sampling point plate, showing no bromide remaining, the reaction is complete; naturally cooled to room temperature, filtered, the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85 ° C), passed through neutral silica gel Column, obtain target product, HPLC purity 99.1%, yield 71.5%;

[0153] Elemental analysis structure (molecular formula C 52 h 35 NO): Theoretical C, 90.54; H, 5.11; N, 2.03; O, 2.32; Tested: C, 90.53; H, 5.13; N, 2.01;

[0154] HPLC-MS: The molecular weight of the material is 689.27, and the measured molecular weight is 689.55.

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Abstract

The invention relates to an organic compound containing 9,9'-spirobifluorene as a core and an application of the organic compound in an OLED (organic light emitting diode) device. The general structural formula of the organic compound is shown in the general formula (1). The provided organic compound has high glass transition temperature, high molecular thermal stability, proper HOMO and LUMO energy levels and higher Eg. By means of structural optimization of the device, photoelectric performance of the OLED device can be effectively improved, and the service life of the OLED device can be effectively prolonged.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an organic compound with 9,9'-spirobifluorene as the core and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/08C07D221/18C07D241/38C07D265/34C07D279/36C07D401/04C07D401/14C07D403/04C07D405/12C07D405/14C07D413/04C07D413/14C07D417/04C07D471/04C07D471/06C07D487/04C07D487/06C07D491/048C07D491/052C07D491/147C07D491/153C07D498/04C07D498/06C07D498/14C07D513/04C07D513/06C07D519/00H01L51/54
CPCC07D219/08C07D221/18C07D241/38C07D265/34C07D279/36C07D401/04C07D401/14C07D403/04C07D405/12C07D405/14C07D413/04C07D413/14C07D417/04C07D471/04C07D471/06C07D487/04C07D487/06C07D491/048C07D491/052C07D491/147C07D491/153C07D498/04C07D498/06C07D498/14C07D513/04C07D513/06C07D519/00H10K85/624H10K85/636H10K85/654H10K85/657H10K85/6572
Inventor 唐丹丹张兆超李崇张小庆王立春
Owner JIANGSU SUNERA TECH CO LTD
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