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Xanthenes organic compound and application thereof to OLED (Organic Light Emitting Diode)

An organic compound, xanthene technology, applied in the field of xanthene organic compounds and its application in organic electroluminescent devices, can solve the problems of different performance, achieve stable three-dimensional structure, improve current efficiency and lifespan , Improve the effect of composite efficiency

Active Publication Date: 2017-12-29
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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  • Xanthenes organic compound and application thereof to OLED (Organic Light Emitting Diode)
  • Xanthenes organic compound and application thereof to OLED (Organic Light Emitting Diode)
  • Xanthenes organic compound and application thereof to OLED (Organic Light Emitting Diode)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Synthesis of Intermediate I and Intermediate II: a1. When L represents a single bond, synthesis of Intermediate I-1:

[0045]

[0046] (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 , Heating to 40°C and stirring until the solution turns from yellow to colorless, and then heating the above-mentioned mixed solution to 60-90°C, stirring and reacting for 3 to 5 hours, no magnesium powder remains, the reaction is complete, and the Grignard reagent intermediate V is generated; The molar ratio of the raw material U to Mg is 1:1.0~1.2; I 2 The molar ratio with raw material U is 0.006~0.02:1;

[0047] (2) Weigh out Xanthone and dissolve it with dry THF; under an inert atmosphere, add dropwise the above-mentioned format reagent intermediate V, and stir the resulting mixed solution at 60-90°C for 10-24 hours to generate a large amount of white precipitate , Then coo...

Embodiment 2

[0079] Example 2: Synthesis of Compound 3:

[0080]

[0081] In a 250mL three-necked flask, add 0.01mol of intermediate M1 and 0.015mol of raw material N1 under a nitrogen atmosphere, dissolve with a mixed solvent (90ml of toluene, 45ml of ethanol), and then add 0.03mol of Na 2 CO 3 Aqueous solution (2M), stirring with nitrogen for 1 hour, then adding 0.0001mol Pd(PPh 3 ) 4 , Heating and refluxing for 15 hours, sampling point plate, the reaction is complete. Naturally cooling, filtering, rotating the filtrate, and passing through a silica gel column to obtain the target product with a purity of 99.2% and a yield of 75.4%. Elemental analysis structure (molecular formula C 49 H 31 NO 3 ): Theoretical value C, 86.32; H, 4.58; N, 2.05; O, 7.04; Test value: C, 86.33; H, 4.57; N, 2.07; O, 7.03. ESI-MS(m / z)(M + ): The theoretical value is 681.23, and the measured value is 681.52.

Embodiment 3

[0082] Example 3: Synthesis of Compound 7:

[0083]

[0084] In a 250ml three-necked flask, add 0.01mol of intermediate M2 and 0.015mol of raw material N2 under a nitrogen atmosphere, dissolve with a mixed solvent (90ml of toluene, 45ml of ethanol), and then add 0.03mol of Na 2 CO 3 Aqueous solution (2M), stirring with nitrogen for 1 hour, then adding 0.0001mol Pd(PPh 3 ) 4 , Heating and refluxing for 15 hours, sampling point plate, the reaction is complete. Natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain the target product with a purity of 98.9% and a yield of 76.2%. Elemental analysis structure (molecular formula C 47 H 29 NO 2 S): Theoretical value C, 84.03; H, 4.35; N, 2.08; O, 4.76; S, 4.77; Test value: C, 84.02; H, 4.34; N, 2.09; O, 4.77; S, 4.78. ESI-MS(m / z)(M + ): The theoretical value is 671.19, and the measured value is 671.41.

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Abstract

The invention relates to a xanthenes organic compound and application thereof to OLED (Organic Light Emitting Diode). According to the structure of the compound, xanthenes are connected with a carbazole cyclic structure through carbon-carbon bonds. Due to carbon-carbon connection, the chemical stability of a material is improved, living position exposure of branch chain groups is avoided, and the whole molecules are of a relatively large rigid structure, and a high triplet state energy stage (T1) is achieved; in addition, large steric hindrance is achieved, rotation is not easily caused, and a relatively stable three-dimensional structure is achieved, so that the compound has relatively high glass transition temperature and molecular thermal stability; in addition, distribution positions of HOMO (Highest Occupied Molecular Orbital ) and LUMO (Lowest Unoccupied Molecular Orbital) of the compound provided by the invention are separated from each other, so that appropriate HOMO and LUMO energy grades are achieved; therefore, after the compound provided by the invention is applied to an OLED device, the light emission efficiency of the device is improved, and the service life of the device is prolonged.

Description

Technical field [0001] The present invention relates to the field of semiconductor technology, in particular to a xanthene organic compound and its application in organic electroluminescent devices. Background technique [0002] Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products as well as new lighting products. It is expected to replace the existing liquid crystal display and fluorescent lighting, and has a broad 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 different functional materials are superimposed on each other according to their uses to form an OLED light-emitting device. The OLED light-emitting device is a current device. When a voltage is applied to the electrodes at its two ends and the positive and negative charges i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/056C07D491/052C07D497/04C07D498/04C07D495/04C07D405/04C07D471/04C07D513/04C07D487/04C07D405/14C07D409/14C07D405/10C07D491/044C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D405/04C07D405/10C07D405/14C07D409/14C07D471/04C07D487/04C07D491/044C07D491/052C07D491/056C07D495/04C07D497/04C07D498/04C07D513/04C09K2211/1092C09K2211/1088C09K2211/1029C09K2211/1011C09K2211/1007C09K2211/1044C09K2211/1037C09K2211/1033H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/18H10K50/15H10K50/11
Inventor 唐丹丹张兆超张小庆王立春
Owner JIANGSU SUNERA TECH CO LTD
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