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Compound taking spirofluorene alkene structure as core, preparation method and applications thereof

A compound, spirofluorene technology, applied in chemical instruments and methods, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve different problems

Pending Publication Date: 2020-02-25
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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  • Compound taking spirofluorene alkene structure as core, preparation method and applications thereof
  • Compound taking spirofluorene alkene structure as core, preparation method and applications thereof
  • Compound taking spirofluorene alkene structure as core, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Embodiment 1: the synthesis of intermediate B1:

[0081]

[0082] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material 1-1, 0.012mol raw material 2-1, 150ml toluene and stir to mix, then add 5×10-5mol Pd 2 (dba) 3 , 5×10-5mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , obtain target product intermediate B1; HPLC purity 99.37%, yield 73.4%; Elemental analysis structure (molecular formula C 24 h 19 N): theoretical value C, 89.68; H, 5.96; N, 4.36; tested value: C, 89.65; H, 5.99; N, 4.37. ESI-MS (m / z) (M+): The theoretical value is 321.42, and the measured value is 321.58.

Embodiment 2

[0083] Embodiment 2: the synthesis of intermediate C1:

[0084]

[0085] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of intermediate B16, 0.012mol of raw material 3-1, 150ml of toluene and stir to mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , to obtain the target product intermediate X1;

[0086] Under a nitrogen atmosphere, weigh 0.02mol of intermediate X1, 0.012mol of bis(pinacolate) diboron, 0.0002mol of Pd(dppf)Cl 2 1. Dissolve 0.05mol potassium acetate in toluene, react at 100-120°C for 12-24 hours, take a sample point plate, react completely, cool naturally, filter, and rotate the filtrate to obtain a crude product, pass through a ne...

Embodiment 3

[0092] Embodiment 3: the synthesis of compound 1:

[0093]

[0094] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol intermediate B1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , the target product was obtained, the HPLC purity was 99.63%, and the yield was 69.8%. Elemental analysis structure (molecular formula C 50 h 33 N): theoretical value: C, 92.70; H, 5.13; N, 2.16; test value C, 92.66; H, 5.22; N, 2.12. HPLC-MS: The molecular weight of the material is 647.82, and the measured molecular weight is 647.35.

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Abstract

The invention discloses a compound taking a spirofluorene alkene structure as a core, a preparation method and applications thereof, wherein the structure of the compound is shown as a general formula(1). According to the invention, the compound has strong hole transport capability, wherein the hole injection and transport performance is improved under a proper HOMO energy level; under a proper LUMO energy level, the electron blocking effect is achieved so as to improve the recombination efficiency of excitons in a light-emitting layer; and with the application of the compound as the light-emitting functional layer material of an OLED light-emitting device, the utilization rate and the radiation efficiency of excitons can be effectively improved by matching with the branched chains in therange of the invention.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound containing spirofluorene, a preparation method thereof and an application in an organic electroluminescence device. 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. 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 li...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07C211/54C07D307/91C07D209/86C07D311/80C07D311/96C07D221/20C07D307/94C07D405/12C07D401/12C07D471/04C07D307/77C09K11/06H01L51/50H01L51/54
CPCC07C211/61C07C211/54C07D307/91C07D209/86C07D311/80C07D311/96C07D221/20C07D307/94C07D405/12C07D401/12C07D471/04C07D307/77C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1088H10K85/624H10K85/615H10K85/631H10K85/636H10K85/626H10K85/633H10K85/657H10K85/6574H10K85/6572H10K50/11H10K2101/40H10K50/18H10K50/15
Inventor 张宇阳李崇张小庆王芳
Owner JIANGSU SUNERA TECH CO LTD
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