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Fluorene-containing organic compound as well as preparation method and application thereof in OLED (organic light emitting diode) device

A technology of organic compounds and bromides, applied in the field of organic optoelectronic materials, can solve different problems

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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  • Fluorene-containing organic compound as well as preparation method and application thereof in OLED (organic light emitting diode) device
  • Fluorene-containing organic compound as well as preparation method and application thereof in OLED (organic light emitting diode) device
  • Fluorene-containing organic compound as well as preparation method and application thereof in OLED (organic light emitting diode) device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0145] Embodiment 1: the synthesis of compound 1:

[0146] synthetic route:

[0147]

[0148] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol raw material B1, 150ml toluene and stir to mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, 0.03mol of sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no remaining bromide, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated until there was no distillate , through a neutral silica gel column to obtain the target product, with a HPLC purity of 99.1% and a yield of 67.3%;

[0149] Elemental analysis structure (molecular formula C 64 h 54 N 2 ): theoretical value C, 90.31; H, 6.39; N, 3.29; test value: C, 90.31; H, 6.36; N, 3.33.

[0150] HPLC-MS: The molecular weight of the material is 850.43, and the measured molecular weight is 850.49.

Embodiment 2

[0151] Embodiment 2: the synthesis of compound 5:

[0152] synthetic route:

[0153]

[0154] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol raw material B2, 150ml toluene and stir to mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, 0.03mol of sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no remaining bromide, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated until there was no distillate , through a neutral silica gel column to obtain the target product, with a HPLC purity of 99.1% and a yield of 66.8%;

[0155] Elemental analysis structure (molecular formula C 58 h 40 N 2 O): Theoretical value C, 89.20; H, 5.16; N, 3.59; O, 2.05; Test value: C, 89.3; H, 5.15; N, 3.61.

[0156] HPLC-MS: The molecular weight of the material is 780.31, and the measured molecular weight is 780.6...

Embodiment 3

[0157] Embodiment 3: the synthesis of compound 11:

[0158] synthetic route:

[0159]

[0160] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol raw material B3, 150ml toluene and stir to mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, 0.03mol of sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no remaining bromide, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated until there was no distillate , through a neutral silica gel column to obtain the target product, with a HPLC purity of 99.3% and a yield of 62.7%;

[0161] Elemental analysis structure (molecular formula C 58 h 40 N 2 O): theoretical value C, 89.20; H, 5.16; N, 3.59; O, 2.05; test value: C, 89.21; H, 5.15; N, 3.59;

[0162] HPLC-MS: The molecular weight of the material is 780.31, and the measured molecular weight is 780...

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Abstract

The invention discloses a fluorene-containing organic compound. The organic compound has the structure formula shown in the general formula (1). The compound has higher glass transition temperature and molecular heat stability, proper HOMO and LUMO energy levels and higher Eg, the photoelectric property of an OLED (organic light emitting diode) device can be effectively improved and the service life of the OLED device can be effectively prolonged through structure optimization of the device.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a compound material containing a fluorene structure as a central skeleton, a preparation method thereof and an application in the field of OLEDs. 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 el...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18C07D491/052C07D491/048C07D401/04C07D471/04C07D471/06C07D413/04C07D417/04C07D241/38C07D487/06C07D491/056C07D498/06C07D413/10C07D513/04C07D279/22C07D405/14C07D219/08C07D401/14C07D413/14C07D265/38C07D265/34C07D403/04C07D401/10C07D405/12C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D219/08C07D221/18C07D241/38C07D265/34C07D265/38C07D279/22C07D401/04C07D401/10C07D401/14C07D403/04C07D405/12C07D405/14C07D413/04C07D413/10C07D413/14C07D417/04C07D471/04C07D471/06C07D487/06C07D491/048C07D491/052C07D491/056C07D498/06C07D513/04C09K2211/1088C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1014C09K2211/1022C09K2211/1011C09K2211/1007C09K2211/1029H10K85/649H10K85/631H10K85/653H10K85/636H10K85/626H10K85/633H10K85/654H10K85/6574H10K85/6572H10K50/00H10K2102/00H10K2102/301
Inventor 王立春张小庆李崇张兆超唐丹丹
Owner JIANGSU SUNERA TECH CO LTD
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