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Dimethyl anthracene organic compound, and application thereof on organic light-emitting device

A technology for electroluminescent devices and organic compounds, applied in organic chemistry, electro-solid devices, electrical components, etc., can solve problems such as different performances, and achieve the effects of stable three-dimensional structure, balanced distribution, and reduced energy loss

Active Publication Date: 2018-02-13
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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  • Dimethyl anthracene organic compound, and application thereof on organic light-emitting device
  • Dimethyl anthracene organic compound, and application thereof on organic light-emitting device
  • Dimethyl anthracene organic compound, and application thereof on organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: the synthesis of intermediate I and intermediate II: a1. When L is represented as a single bond, the synthesis of intermediate I-1:

[0047]

[0048] (1) Weigh the raw materials U and Mg powder, and dissolve them with dry tetrahydrofuran (THF); under an inert atmosphere, add a small amount of catalyst I 2 , heated to 40°C and stirred until the solution changed from yellow to colorless, then heated the above mixed solution to 60-90°C, stirred and reacted for 3-5 hours, no magnesium powder remained, the reaction was complete, and Grignard reagent intermediate V was generated; The mol ratio of described raw material U and Mg is 1:1.0~1.2; I 2 The molar ratio with raw material U is 0.006~0.02:1;

[0049] (2) Weigh 10,10-dimethylanthrone and dissolve it in dry THF; under an inert atmosphere, add the above-mentioned Grignard reagent intermediate V dropwise, and stir the resulting mixed solution at 60-90°C for 10-24 Hours, a large amount of white precipitate...

Embodiment 2

[0081] Embodiment 2: the synthesis of compound 2:

[0082]

[0083] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol of intermediate M1, 0.015mol of raw material N1, dissolve in a mixed solvent (90ml of toluene, 45ml of ethanol), and then add 0.03mol of Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0001mol Pd(PPh 3 ) 4 , heating to reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.3% and a yield of 78.2%. Elemental analysis structure (molecular formula C 46 h 33 NO 2 ): theoretical value C, 87.45; H, 5.27; N, 2.22; 0, 5.06; test value: C, 87.46; ESI-MS(m / z)(M + ): The theoretical value is 631.25, and the measured value is 631.46.

Embodiment 3

[0084] Embodiment 3: the synthesis of compound 6:

[0085]

[0086] In a 250ml three-neck flask, under an atmosphere of nitrogen gas, add 0.01mol intermediate M2, 0.015mol raw material N2, dissolve with a mixed solvent (90ml toluene, 45ml ethanol), and then add 0.03mol Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0001mol Pd(PPh 3 ) 4 , heating to reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.4% and a yield of 79.2%. Elemental analysis structure (molecular formula C 59 h 43 NO): theoretical value C, 90.62; H, 5.54; N, 1.79; 0, 2.05; test value: C, 90.61; ESI-MS(m / z)(M + ): The theoretical value is 781.33, and the measured value is 781.55.

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Abstract

The invention relates to a dimethyl anthracene organic compound, and application thereof on an organic light-emitting device. A structure of the compound is characterized in that dimethyl anthracene is connected with a carbazole parallel loop structure through a carbon-carbon bond; with the carbon-carbon bond connection, the chemical stability of the material is improved, and an active position ofa branch perssad is prevented from being exposed; in addition, the whole molecule is of a larger rigid structure, has a high triplet state energy level (T1), and is large in steric hindrance, not easy to rotate, and more stable in three-dimensional space structure, so that the compound has higher glass state temperature and molecular heat stability; in addition, distribution positions of HOMO andLUMO of the compound provided by the invention are separated, so that the compound has appropriate HOMO and LUMO energy levels; therefore, after the compound provided by the invention is applied to the OLED (Organic Light-emitting Diode) device, the light-emitting efficiency and the service life of the device can be effectively improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a dimethyl anthracene organic compound 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. 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. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and the positive and neg...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/056C07D491/052C07D497/04C07D498/04C07D495/04C07D209/80C07D209/94C07D471/04C07D513/04C07D487/04C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D209/80C07D209/94C07D471/04C07D487/04C07D491/052C07D491/056C07D495/04C07D497/04C07D498/04C07D513/04C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1018C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092H10K85/615H10K85/6574H10K85/657H10K85/6572H10K50/00H10K50/18H10K50/15H10K50/11
Inventor 唐丹丹张兆超张小庆王立春
Owner JIANGSU SUNERA TECH CO LTD
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