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Pyrene-containing organic compound and application thereof

An organic compound, electromechanical technology, applied in the fields of organic chemistry, chemical instruments and methods, electrical components, etc., can solve different problems, achieve high glass transition temperature, improve optoelectronic properties, and optimize the effect of structure

Pending Publication Date: 2020-09-15
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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  • Pyrene-containing organic compound and application thereof
  • Pyrene-containing organic compound and application thereof
  • Pyrene-containing organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Embodiment 1: the synthesis of intermediate B1:

[0078]

[0079] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material 1-1, 0.012mol raw material 2-1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , obtain target product intermediate B1; HPLC purity 99.37%, yield 73.4%; Elemental analysis structure (molecular formula C 30 h 22 N 2 ): theoretical value C, 87.77; H, 5.40; N, 6.82; test value: C, 87.79; H, 5.39; N, 6.81. ESI-MS (m / z) (M+): theoretical value 410.18, found value 410.31.

[0080] The synthetic raw materials of intermediate B required in the embodiment are shown in Table 1:

[0081] Table 1 ...

Embodiment 2

[0086] Embodiment 2: the synthesis of compound 1:

[0087]

[0088] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of reactant A1, 0.012mol of intermediate B1, 150ml of toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , the target product was obtained, the HPLC purity was 99.73%, and the yield was 72.9%. Elemental analysis structure (molecular formula C 46 h 30 N 2 ): theoretical value: C, 90.46; H, 4.95; N, 4.59; test value C, 90.48; H, 4.94; N, 4.58. HPLC-MS: The molecular weight of the material is 610.24, and the measured molecular weight is 610.39.

Embodiment 3

[0089] Embodiment 3: the synthesis of compound 6:

[0090]

[0091] Prepare by the synthetic method of compound 1 in embodiment 2, difference is to replace intermediate B1 with intermediate B2; Elemental analysis structure (molecular formula C 50 h 32 N 2 ): Theoretical value: C, 90.88; H, 4.88; N, 4.24; Test value: C, 90.87; H, 4.87; N, 4.26. HPLC-MS: The molecular weight of the material is 660.26, and the measured molecular weight is 660.34.

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Abstract

The invention relates to a pyrene-containing organic compound and application thereof, and belongs to the technical field of semiconductors, wherein structure of the compound is represented by a general formula (1). The compound provided by the invention has relatively strong hole transport capability, and the hole injection and transport performance is improved under a proper HOMO energy level; under the proper LUMO energy level, the electron blocking effect is achieved, and the recombination efficiency of excitons in the light-emitting layer is improved; and when the compound is applied to an OLED device, high film layer stability can be kept through device structure optimization, the photoelectric property of the OLED device can be effectively improved, and the service life of the OLEDdevice can be effectively prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a pyrene-containing organic compound and its application. 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 both ends of the OLED light-emitting device, and the positive and negative charges in the organic laye...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D471/04C07D491/048C07D405/12C07D401/12C07D409/12C07D417/12C09K11/06H01L51/54
CPCC07D209/86C07D471/04C07D491/048C07D405/12C07D401/12C07D409/12C07D417/12C09K11/06C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1037C09K2211/1033C09K2211/1011C09K2211/1007C09K2211/1014C09K2211/1022H10K85/622H10K85/636H10K85/633H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K85/657
Inventor 王芳李崇吴秀芹谢丹丹
Owner JIANGSU SUNERA TECH CO LTD
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