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Fused ring aryl compound, electronic device and application thereof

A technology for condensed ring aromatic groups and electronic devices, applied in the field of optoelectronic materials, can solve the problems of short lifespan of P-doped materials, and achieve the effects of reducing annihilation, enhancing electron injection and transport capabilities, and improving stability

Pending Publication Date: 2020-03-27
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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  • Fused ring aryl compound, electronic device and application thereof
  • Fused ring aryl compound, electronic device and application thereof
  • Fused ring aryl compound, electronic device and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040] Synthesis of intermediate 1-P-1: In a 50 ml three-necked flask, 2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetraketone (5.03 g, 0.01 mol ), N-methylpyrrolidone (NMP, 20 ml), sodium carbonate (0.01mol), K 4 [Fe(CN) 6 ](2.5mmol),Pd(OAc) 2 (1mmol), heated to 120 degrees Celsius, stirred for 20 hours, after the reaction was completed, cooled to room temperature, filtered, removed the solvent, and the crude product was passed through a chromatographic column (n-hexane: ethyl acetate: dichloromethane=10:2:2) , to obtain intermediate 1-P-1 (1.8 g, yield 63%).

[0041] Synthesis of P-1:

[0042] The first step: in a 50 ml three-necked flask, add 1-P-1 (2.9 grams, 1 equivalent, 0.01mol), urea (2.4 grams, 4 equivalents), and ethanol (10 milliliters) to reflux for 10 hours under a nitrogen atmosphere. After the reaction was completed, cooled to room temperature, quenched by adding 10 ml of water, extracted with ethyl acetate (20 ml*3), dried over anhydrous sodium sulfat...

Embodiment 2

[0046]

[0047] Synthesis of P-4: In a 50 ml three-necked flask, add 1,4,5,8-tetrafluoro-2,3,6,7-tetracyanonaphthalene (3.0 g, 0.01 mol) under nitrogen protection, di Amino maleic dicyanide (2.16 g, 0.02 mol), DMF (10 ml), sodium tert-butoxide (1 mmol), heated to 120 ° C, stirred for 5 hours, after the reaction was completed, quenched with water, extracted with dichloromethane , the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed, and the product was beaten three times with (n-hexane: dichloromethane: acetonitrile=10:2:3), and once with acetonitrile to obtain P-4 (1.51 grams, yield 35%) .

[0048] Elemental Analysis: C 22 N 12 Theoretical: C, 61.12; N, 38.88; Found: C, 61.16; N, 38.84; HRMS (ESI) m / z(M): Theoretical: 432.0369; Found: 432.0361.

Embodiment 3

[0050] Fabrication of organic electroluminescent devices:

[0051] The ITO transparent substrate is placed in the evaporation equipment, wherein ITO (indium tin oxide) is used as the anode layer 1, and the 10nm hole injection layer 2, the 100nm hole transport layer 3 (HTL), and the 50nm organic light-emitting layer 4 ( EML), 40nm electron transport layer 5 (ETL), 1nm electron injection layer 6 (EIL), 80nm cathode layer 7, where N,N'-diphenyl-N,N'-(1-naphthyl)- 1,1'-biphenyl-4,4'-diamine as hole transport layer 3, 3 wt% Ir(piq) 3 : CBP is used as the organic light-emitting layer 4, BPhen is used as the electron transport layer 5, LiF is used as the electron injection layer 6, and Al is used as the cathode layer 7 so that the device is formed as figure 1 The specific structure shown.

[0052] step:

[0053] (1) Substrate cleaning: the transparent motor substrate coated with ITO is ultrasonically treated in an aqueous cleaning agent (composition and concentration of the aqueou...

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Abstract

The present invention provides a fused ring aryl compound, an electronic device and application thereof. The fused ring aryl compound has a structure represented by a formula (I), n is 1 or 2, R1, R2and a ring B are connected through a single bond or a double bond, and R1 to R6 are electron withdrawing groups. According to the fused ring aryl compound provided by the invention, a parent nucleus structure is a non-planar structure (a three-dimensional structure), the stacking between molecules is avoided, the annihilation generated by high-energy excitons is reduced, an anode is promoted to inject holes into a hole transport layer, the generation of joule heat is avoided, the stacking and crystallization of molecules of the hole transport layer are avoided, and the service life of a deviceis prolonged. A substituent group is an electron withdrawing group such that the LUMO energy level of the compound is -4.6 to -6.0 eV, and the compound can be used as a P-doped material.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a condensed ring aromatic compound, an 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: hole injec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/06H01L51/50H01L51/54H01L51/42H01L51/46H01L51/05H01L51/30
CPCC07D487/06H10K85/654H10K85/6572H10K10/00H10K30/00H10K50/00Y02E10/549
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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