Condensed-ring aryl compound, organic electronic device, and application thereof
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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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[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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Embodiment 1
[0049]
[0050] Synthesis of intermediate 1-P-1: In a 250 ml three-necked flask, 1-bromo-2,3,5,6-tetrafluoro-4-nitrobenzene (27.3 g, 1 equivalent, 0.1 mol), 2,3-diaminomaledicyanide (21.60 grams, 2 equivalents, 0.2mol), sodium tert-butoxide (4 equivalents, 0.4mol), ethanol (80 milliliters), reflux, stir 12 hours, react After completion, cool down to room temperature, add 10 ml of ice water to quench, extract with dichloromethane, rotate the concentrate, recrystallize from ethanol, beat with acetonitrile for 3 times to obtain intermediate 1-P-1 (16.2 g, yield 40%) .
[0051] Intermediate 2-P-1: Add intermediate 1-P-1 (4.40 g, 1 equivalent, 0.01 mol), 4-bromo-2,3 , 5,6-tetrafluoropyridine (4.58 grams, 2 equivalents), tetrahydrofuran (THF, 20 milliliters), under the condition of -78°C, slowly add n-butyllithium (2 equivalents), after the addition, it was raised to room temperature and stirred for 4 Hours, after the reaction was completed, 10 ml of water was added dropwise to...
Embodiment 2
[0057]
[0058] Synthesis of P-2: same as the synthesis of intermediate 1-P-1, the difference lies in the substitution of 1,2,4,5-tetrafluoro-3,6-dinitrobenzene (24 g, 1 equivalent, 0.1 mol) 1-bromo-2,3,5,6-tetrafluoro-4-nitrobenzene to obtain compound P-2 (19.0 g, yield 51%).
[0059] Elemental Analysis: C 14 N 10 f 4 Theoretical: C, 45.18; N, 37.63; Found: C, 45.21; N, 37.60; HRMS (ESI) m / z(M): Theoretical: 372.0104; Found: 372.0109.
Embodiment 3
[0061]
[0062] The synthesis of P-3: the same as the synthesis of intermediate 1-P-1, the difference is that 1,2,4,5-tetrafluoro-3,6-dicyanobenzene (20 g, 1 equivalent, 0.1 mol) substituted the compound 1-bromo-2,3,5,6-tetrafluoro-4-nitrobenzene to obtain compound P-3 (14.6 g, yield 44%).
[0063] Elemental Analysis: C 16 N 10 Theoretical: C, 57.84; N, 42.16; Found: C, 57.87; N, 42.13; HRMS (ESI) m / z(M): Theoretical: 332.0307; Found: 332.0312.
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Abstract
The invention relates to a condensed-ring aryl compound, an organic electronic device, and an application thereof, wherein the condensed-ring aryl compound has the structure as the formula (I), wherein n is an integer of 0 to 5, X1, X2, Y1, Y2 are independently selected from a combination of a connecting bond, N and CR5, any one of the groups of R1 to R5 is independently connected to a ring A anda ring B via a single bond or a double bond, and/or, any adjacent two among the R1 to R5 form a ring C, being an electron-withdrawing ring, and the R1 to R5 are electron-withdrawing groups. The structure is a non-planar structure, so that annihilation due to high-energy exciton is reduced, and the positive electrode is promoted to inject a cavity into a cavity transport layer, and stack and crystallization of molecules in the cavity transport layer are avoided and service life of the device is prolonged. The main nuclear has a rigid structure, so that the stability of the device is enhanced. The substituent groups are electron-withdrawing groups, so that 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...
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