Condensed-ring aryl compound, organic electronic device, and application thereof

A technology of fused-ring aromatic groups and compounds, which is applied in the field of optoelectronic materials and can solve the problems of short lifespan of P-doped materials

Inactive Publication Date: 2020-03-10
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Therefore, the technical problem to be solved in the present invention is to overcome the short life of P-doped materials in the prior art, thereby providing a fused-ring aryl compound

Method used

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  • Condensed-ring aryl compound, organic electronic device, and application thereof
  • Condensed-ring aryl compound, organic electronic device, and application thereof
  • Condensed-ring aryl compound, organic electronic device, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049]

[0050] Synthesis of intermediate 1-P-1: In a 250 ml three-necked flask, add 4-bromo-2,3,5,6-tetrafluorobenzonitrile (25.29 g, 1 equivalent, 0.1 mol) under nitrogen protection, Tetrahydrofuran (80 milliliters), under the condition of -78 degrees Celsius, slowly add n-butyl lithium (0.1mol) dropwise. :1-5:1), the intermediate 1-P-1 (13.22 g, yield: 38%) was obtained.

[0051] Synthesis of P-1: In a 100 ml three-necked flask, under nitrogen protection, add intermediate 1-P-1 (3.48 g, 1 equivalent, 0.01 mol), ethanol (30 ml), 2,3-diaminocis-butyl Dicyandiamide (4.32 g), slowly added sodium tert-butoxide (8 equivalents), refluxed for 12 hours, after the reaction was completed, cooled to room temperature, quenched with 10 ml of ice water, extracted with dichloromethane, the concentrate was rotary evaporated, beaten (n-hexane: dichloromethane: acetonitrile = 10:3:2) three times, acetonitrile recrystallization once to obtain P-1 (2.57 g, yield 42%).

[0052] Elemental An...

Embodiment 2

[0054]

[0055] The synthesis of intermediate 1-P-2: the same as the synthesis of intermediate 1-P-1, the difference is that 2-bromo-3,4,5,6-tetrafluorobenzonitrile is used instead of 4-bromo-2,3, 5,6-tetrafluorobenzonitrile to obtain intermediate 1-P-2 (11.83 g, yield 34%).

[0056] Synthesis of P-2: Same as the synthesis of P-1, except that intermediate 1-P-2 was used instead of intermediate 1-P-1 to obtain P-2 (2.75 g, yield 45%).

[0057] Elemental Analysis: C 30 N 18 Theoretical: C, 58.83; N, 41.17; Found: C, 58.80; N, 41.20; HRMS (ESI) m / z(M): Theoretical: 612.0553; Found: 612.0560.

Embodiment 3

[0059]

[0060]The synthesis of intermediate 1-P-3: the synthesis of intermediate 1-P-1, the difference is that 1-bromo-2,3,5,6-tetrafluoro-4-nitrobenzene (27.2 grams, 1 equivalent , 0.1mol) instead of 4-bromo-2,3,5,6-tetrafluorobenzonitrile to obtain intermediate 1-P-3 (17.8 g, yield 46%).

[0061] The synthesis of intermediate 2-P-3: the same as the synthesis of P-1, the difference is that intermediate 1-P-3 (3.9 g, 1 equivalent) is used instead of intermediate 1-P-1 to obtain intermediate 2-P -3 (3.0 g, 46% yield).

[0062] Synthesis of P-3: In a 50 ml three-neck flask, under nitrogen protection, add intermediate 2-P-3 (6.5 g, 1 equivalent, 0.01 mol), 4,7,13,16,21,24-hexaoxo -1,10-diazabicyclo[8.8.8]hexacane (0.01mol), DMF (15 milliliters), stirred at 150°C for 1 hour, cooled to room temperature after the reaction was completed, added a mixture of water and dichloromethane ( 5:3), the product entered the dichloromethane layer, and after separation, (n-hexane:dichlorome...

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Abstract

The invention provides a condensed-ring aryl compound, an organic electronic device, and an application thereof. The compound has the structure represented as the formula (I) or (II), wherein X1, X2 and Y1 are independently selected from a combination of a connecting bond, N and CR6, the ring A and the ring B are in a conjugated structure, any one of the R1 to R4 and the R6 are independently connected to the ring A the ring B via a single bond or a double bond, and/or the any adjacent two among the R1 to R4 and the R6 form a ring C, being an electron-withdrawing ring, the R5 is selected from aconnection bond, R7-substituted or -non-substituted C6-C30 aryl groups, and R7-substituted or -non-substituted C2-C30 heteroaryl groups, and the R1 to R4, R6 and R7 are electron-withdrawing groups. The compound is free of intramolecular stacking and can prolong service life of the device, wherein the substituent groups are electron-withdrawing groups, and the compound has LUMO energy level of -4.6 to -6.0 eV. The compound can serve as a P-doping material.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a condensed ring aromatic compound, an organic electronic device and applications thereof. Background technique [0002] Compared with inorganic electroluminescent devices (electro luminescence devices, ELDs), organic light-emitting diodes (OLEDs) have the advantages of high brightness, fast response, wide viewing angle, simple process, high color purity, and can be realized by The advantages of full-color display from blue light to red light region, flexibility, etc., have broad application prospects in the field of display and lighting, and have attracted more and more attention. [0003] OLED devices in the prior art usually include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and are matched with suitable electrodes. The above layers are composed of the following materials: ho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07D241/36C09K11/06H01L51/50H01L51/54H01L51/05H01L51/30H01L51/46H01L51/42
CPCC07D519/00C07D241/36C09K11/06C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1074H10K85/626H10K85/615H10K85/654H10K85/6572H10K10/00H10K30/00H10K50/17Y02E10/549
Inventor 谢坤山蔡烨丁欢达魏定纬陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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