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Compound containing aza-spirofluorene and nitrogen-containing hexa-heterocycle and application of compound in organic light emission diode device

An electroluminescent device, a technology of six-membered heterocycles, applied to organic electroluminescence devices, in the field of compounds containing azaspirofluorene and nitrogen-containing six-membered heterocycles, which can solve problems such as differences and achieve difficulty in aggregation , good industrialization prospects, good film-forming effect

Pending Publication Date: 2017-08-18
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Compound containing aza-spirofluorene and nitrogen-containing hexa-heterocycle and application of compound in organic light emission diode device
  • Compound containing aza-spirofluorene and nitrogen-containing hexa-heterocycle and application of compound in organic light emission diode device
  • Compound containing aza-spirofluorene and nitrogen-containing hexa-heterocycle and application of compound in organic light emission diode device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the synthesis of intermediate A:

[0040]

[0041](1) Under a nitrogen atmosphere, weigh raw material B and dissolve it in tetrahydrofuran, then add raw material C and tetrakis(triphenylphosphine)palladium, stir the mixture, then add potassium carbonate aqueous solution, and mix the above-mentioned reactants at the reaction temperature At 70-90°C, heat to reflux for 5-20 hours. After the reaction, cooling and adding water, the mixture was extracted with dichloromethane, the extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, the obtained residue was purified by silica gel column to obtain intermediate I;

[0042] The molar ratio of raw material B to raw material C is 1:1.0 to 1.5, the molar ratio of tetrakis(triphenylphosphine) palladium to raw material B is 0.001 to 0.02:1, and the molar ratio of potassium carbonate to raw material B is 1.0 to 2.0:1 , The ratio of THF dosage to raw material B is 1g:10~30m...

Embodiment 2

[0065] Embodiment 2: the synthesis of compound 2:

[0066]

[0067] In a 250mL three-necked flask, nitrogen was introduced, 0.01mol of raw material A1, 150ml of THF, 0.015mol of intermediate A1, 0.0001mol of tetrakis(triphenylphosphine) palladium were added, stirred, and then 0.02mol of K 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 15 hours, sampled and plated, the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain the target compound with a HPLC purity of 99.1% and a yield of 77.3%. Elemental analysis structure (molecular formula C 44 h 27 N 5 ): theoretical value C, 84.46; H, 4.35; N, 11.19; test value: C, 84.47; H, 4.36; N, 11.17. ESI-MS(m / z)(M + ): The theoretical value is 625.23, and the measured value is 625.57.

Embodiment 3

[0068] Embodiment 3: the synthesis of compound 4:

[0069]

[0070] In a 250mL three-necked flask, feed nitrogen, add 0.01mol of raw material A1, 150ml of THF, 0.015mol of intermediate A2, 0.0001mol of tetrakis(triphenylphosphine)palladium, stir, and then add 0.02mol of K 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 15 hours, sampled and plated, the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain the target compound with an HPLC purity of 99.3% and a yield of 71.9%. Elemental analysis structure (molecular formula C 50 h 31 N 5 ): theoretical value C, 85.57; H, 4.45; N, 9.98; test value: C, 85.57; H, 4.44; N, 9.99. ESI-MS(m / z)(M + ): The theoretical value is 701.26, and the measured value is 701.62.

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Abstract

The invention discloses a compound containing aza-spirofluorene and nitrogen-containing hexa-heterocycle and application of the compound in an organic light emission diode device. The compound contains aza-spirofluorene and aza-hexatomic ring structures, and the spirofluorene structure is provided with two symmetrical Ns; the two radical groups are strong electron radical groups and have the deep HOMO energy level and the high electron mobility, and the compound is suitable for serving as a hole-blocking material or an electron transport material for application; the compound contains the structure of the hole radical group and an electron and a hole which can balance the material, and the material can serve as partial electron type luminous layer main material to use; in addition, the compound radical group is high in rigidity and has the advantages of being not likely to crystallize between molecules or aggregate and having the good film-forming property. After the compound serves as organic light emitting function layer material to be applied to the OLED device, the current efficiency, power efficiency and external quantum efficiency of the device are all greatly improved; meanwhile, the service life of the device is prolonged very obviously.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing azaspirofluorene and a nitrogen-containing six-membered heterocyclic ring, and its application in an organic electroluminescent device. 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. As a current device, when a voltage is applied to the electrodes at bo...

Claims

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Application Information

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IPC IPC(8): C07D471/10C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D471/10C07D519/00C09K2211/1059C09K2211/1044C09K2211/1033C09K2211/1029C09K2211/1007H10K85/615H10K85/626H10K85/654H10K85/657H10K85/6572H10K85/6574
Inventor 张兆超李崇张小庆吴英杰於哲峰
Owner JIANGSU SUNERA TECH CO LTD
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