Organic compound containing 9,9'-spirobifluorene as main body and application of organic compound

An organic compound, spirobifluorene technology, applied in the field of organic optoelectronic materials, can solve problems such as disparity, and achieve the effects of avoiding aggregation, improving current efficiency and life, and reducing efficiency roll-off

Inactive Publication Date: 2018-04-03
VALIANT 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 main body and application of organic compound
  • Organic compound containing 9,9'-spirobifluorene as main body and application of organic compound
  • Organic compound containing 9,9'-spirobifluorene as main body and application of organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Embodiment 1: the synthesis of compound 6:

[0091] synthetic route:

[0092]

[0093] In a 250ml three-neck flask, under nitrogen protection, add 0.01mol 3-bromo-9,9'-spirobifluorene, 0.012mol intermediate A1, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.3%, yield 76.7%;

[0094] Elemental analysis structure (molecular formula C 46 h 31 NO): Theoretical C, 90.02; H, 5.09; N, 2.28; O, 2.61; Tested: C, 90.04; H, 5.07; N, 2.27;

[0095] HPLC-MS: The molecular weight of the material is 613.24, and the measured molecular weight is 613.55.

Embodiment 2

[0096] Embodiment 2: the synthesis of compound 13:

[0097] synthetic route:

[0098]

[0099] 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 0.03mol sodium tert-butoxide, 5× 10 -5 molPd 2 (dba) 3 , 5×10 - 5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.4%, yield 77.9%;

[0100] Elemental analysis structure (molecular formula C 46 h 31 NO): Theoretical C, 90.02; H, 5.09; N, 2.28; O, 2.61; Tested: C, 90.01; H, 5.10; N, 2.27;

[0101] HPLC-MS: The molecular weight of the material is 613.24, and the measured molecular weight is 613.44.

Embodiment 3

[0102] Embodiment 3: the synthesis of compound 31:

[0103] synthetic route:

[0104]

[0105] In a 250ml three-neck flask, under nitrogen protection, add 0.01mol 3-bromo-9,9'-spirobifluorene, 0.012mol intermediate C1, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 5× 10 -5 molPd 2 (dba) 3 , 5×10 - 5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.1%, yield 75.8%;

[0106] Elemental analysis structure (molecular formula C 46 h 31 NO): Theoretical C, 90.02; H, 5.09; N, 2.28; O, 2.61; Tested: C, 90.01; H, 5.07; N, 2.30;

[0107] HPLC-MS: The molecular weight of the material is 613.24, and the measured molecular weight is 613.47.

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Abstract

The invention relates to an organic compound containing 9,9'-spirobifluorene as a main body. The general structural formula of the organic compound is shown as the general formula (1) in the description. According to the organic compound, 9,9'-spirobifluorene is taken as a parent nucleus and linked with symmetric or asymmetric rigid groups, crystallinity of molecules is broken, aggregation among the molecules is avoided, and the organic compound has high glass transition temperature; when the organic compound is applied to an OLED (organic light emitting diode) device, high film stability canbe kept, and the service life of the OLED device can be prolonged.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a compound material with 9,9'-spirobifluorene as the core structure and its application in the OLED field. 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 OLED light...

Claims

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Application Information

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IPC IPC(8): C07D413/10C07D221/18C07D279/14C07D241/38C07D265/34C07D491/048C07D498/04C07D471/04C07D487/04C07D519/00C07D498/06C07D513/06C07D487/06C07D491/153C07D495/14C07D498/14C07D471/14C07D513/14C07D495/04C07D491/147C07D491/052C07D491/056C07D513/04C07D413/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D221/18C07D241/38C07D265/34C07D279/14C07D413/10C07D413/14C07D471/04C07D471/14C07D487/04C07D487/06C07D491/048C07D491/052C07D491/056C07D491/147C07D491/153C07D495/04C07D495/14C07D498/04C07D498/06C07D498/14C07D513/04C07D513/06C07D513/14C07D519/00C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1011C09K2211/1007C09K2211/1029H10K85/615H10K85/624H10K85/656H10K85/654H10K85/657H10K85/6572H10K50/00H10K50/11
Inventor 唐丹丹张兆超李崇张小庆王立春
Owner VALIANT CO LTD
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