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Heterocyclic compound with xanthone as core and preparation method and applications thereof

A technology of heterocyclic compounds and xanthone, which is applied in the field of heterocyclic compounds, can solve the problems of low S1 state radiation transition rate, difficult high exciton utilization rate, high fluorescence radiation efficiency, and efficiency roll-off, etc., to achieve enhanced luminescence Effects of efficiency and service life, polymer thermal stability, and large steric hindrance

Active Publication Date: 2019-11-19
JIANGSU SUNERA TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007]Although TADF materials can achieve 100% exciton utilization in theory, there are actually the following problems: (1) The T1 and S1 states of the designed molecules have strong CT features, very small S1-T1 state energy gap, although a high T1→S1 state exciton conversion rate can be achieved through the TADF process, but at the same time lead to a low S1 state radiation transition rate, so it is difficult to achieve both (or simultaneously) High exciton utilization and high fluorescence radiation efficiency; (2) Even if doped devices have been used to alleviate the quenching effect of T1 exciton concentration, most TADF material devices have a serious efficiency roll-off at high current densities

Method used

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  • Heterocyclic compound with xanthone as core and preparation method and applications thereof
  • Heterocyclic compound with xanthone as core and preparation method and applications thereof
  • Heterocyclic compound with xanthone as core and preparation method and applications thereof

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Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0267] Preparation of Compound S13

[0268]

[0269] 1) Under a nitrogen atmosphere, add 0.1mol of raw material D-1 and 0.3mol of raw material E-1 to a 250mL three-neck flask, add 100mL of 1,4-dioxane to dissolve them, and stir for 30min with nitrogen gas, then add 0.02mol CuI, 0.02mol trans-1,2-diaminocyclohexane, 0.4mol K 3 PO 4 , heated to 110° C., reacted for 24 h, and observed the reaction by thin-layer chromatography (TLC) until the reaction was complete. After naturally cooling to room temperature, NH 4 CO 3 The aqueous solution was extracted with dichloromethane, separated, and the organic phase was rotary evaporated under reduced pressure until there was no fraction. The obtained substance was purified by silica gel column to obtain intermediate F-1 with a purity of 99.8% and a yield of 71.6%.

[0270] Elemental analysis structure (molecular formula C 43 h 29 N 3 ): theoretical value C, 87.88; H, 4.97; N, 7.15; test value: C, 87.86; H, 4.98; N, 7.16. ESI-...

preparation Embodiment 2

[0275] Preparation of Compound S19

[0276]

[0277] 1) Under a nitrogen atmosphere, add 0.1mol of raw material D-1 and 0.3mol of raw material E-1 to a 250mL three-neck flask, add 100mL of 1,4-dioxane to dissolve them, and stir for 30min with nitrogen gas, then add 0.02mol CuI, 0.02mol trans-1,2-diaminocyclohexane, 0.4mol K 3 PO 4 , heated to 110° C., reacted for 24 h, and observed the reaction by thin-layer chromatography (TLC) until the reaction was complete. After naturally cooling to room temperature, NH 4 CO 3 The aqueous solution was extracted with dichloromethane, separated, and the organic phase was rotary evaporated under reduced pressure until there was no fraction. The obtained substance was purified by silica gel column to obtain intermediate F-1 with a purity of 99.8% and a yield of 71.6%.

[0278] Elemental analysis structure (molecular formula C 43 h 29 N 3 ): theoretical value C, 87.88; H, 4.97; N, 7.15; test value: C, 87.86; H, 4.98; N, 7.16. ESI-...

preparation Embodiment 3

[0287] Preparation of Compound S39

[0288]

[0289] 1) Under a nitrogen atmosphere, add 0.2 mol of the prepared intermediate II-1, 0.3 mol of raw material IV-2, 0.15 mol of sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 and 1×10 -4 mol of tri-tert-butylphosphine, then add 150mL of toluene to dissolve it, heat to 100°C, reflux for 24h, observe the reaction by TLC until the reaction is complete. Naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated until there was no fraction. The obtained substance was purified by silica gel column to obtain intermediate A-2 with a purity of 99.3% and a yield of 75.9%.

[0290] Elemental analysis structure (molecular formula C 44 h 30 BrN 3 ): Theoretical C, 77.64; H, 4.44; Br, 11.74; N, 6.17; Found: C, 77.65; H, 4.45; Br, 11.75; N, 6.15. ESI-MS(m / z)(M + ): The theoretical value is 679.16, and the measured value is 679.46.

[0291] 2) Under a nitrogen atmosphere, add 0.1mol of intermediate A-2 to ...

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Abstract

The invention discloses a heterocyclic compound with xanthone as a core and a preparation method and applications thereof, and belongs to the technical field of semiconductors. The structure of the compound provided by the invention is represented by a general formula (I) shown in the description. The invention also discloses the preparation method and the applications of the compound. The compound of the invention has high glass transition temperature and molecular thermal stability and has a suitable HOMO and LUMO energy leves, has a singlet-triplet energy level difference ([delta]Est), andcan be used as a doping material of a light emitting layer of an organic electroluminescent device, thereby improving the luminous efficiency and service life of the device.

Description

technical field [0001] The invention relates to a heterocyclic compound with xanthone as the core, a preparation method and application thereof, and belongs to the technical field of semiconductors. Background technique [0002] Organic electroluminescence (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 phenomenon of organic light emission is an example of the conversion of electric current into visible light by the internal processing of specific organic molecules. The organic light-emitting phenomenon is based on the following mechanism: when an organic material layer is inserted between an anode and a cathode, if a voltage is applied between the two electrodes, electrons and holes are injected from the cathode and anode into th...

Claims

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Application Information

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IPC IPC(8): C07D405/14C09K11/06H01L51/54
CPCC07D405/14C09K11/06C09K2211/1088C09K2211/1029H10K85/6574H10K85/6572
Inventor 李崇唐丹丹张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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