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A compound containing spirodimethylanthrafluorene and its application in organic electroluminescent devices

A technology of spirodimethylanthrafluorene and dimethylfluorenyl, which is applied in the fields of electric solid-state devices, organic chemistry, luminescent materials, etc., can solve different problems, avoid aggregation, significantly improve device life, and facilitate energy transfer Effect

Active Publication Date: 2022-03-29
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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  • A compound containing spirodimethylanthrafluorene and its application in organic electroluminescent devices
  • A compound containing spirodimethylanthrafluorene and its application in organic electroluminescent devices
  • A compound containing spirodimethylanthrafluorene and its application in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Embodiment 1: the synthesis of compound 8:

[0095]

[0096] In a 250ml three-neck flask, under nitrogen protection, add 0.01mol of raw material A1, namely 2'-bromo-10,10-dimethyl-10H-spiro[anthracene-9,9'-fluorene], 0.012mol of raw material B1, 150ml of toluene was stirred and mixed, then 0.03mol sodium tert-butoxide was added, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.3%, yield 84.7%;

[0097] Elemental analysis structure (molecular formula C 52 h 36 N 2 ): theoretical value C, 90.67; H, 5.27; N, 4.07; test value: C, 90.67; H, 5.28; N, 4.05. ESI-MS(m / z)(M + ): The theoretical value is 688.29, and the measured value ...

Embodiment 2

[0098] Embodiment 2: the synthesis of compound 15:

[0099]

[0100] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of raw material A1, namely 2'-bromo-10,10-dimethyl-10H-spiro[anthracene-9,9'-fluorene], 0.012mol of raw material B2, 150ml of toluene was stirred and mixed, then 0.03mol sodium tert-butoxide was added, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.5%, yield 82.9%;

[0101] Elemental analysis structure (molecular formula C 49 h 37 N): theoretical value C, 91.98; H, 5.83; N, 2.19; test value: C, 92.00; H, 5.82; N, 2.18. ESI-MS(m / z)(M + ): The theoretical value is 639.29, and the measured va...

Embodiment 3

[0102] Embodiment 3: the synthesis of compound 16:

[0103]

[0104] The preparation method of compound 16 is the same as that in Example 1, except that raw material B1 is replaced with raw material B3.

[0105] Elemental analysis structure (molecular formula C 52 h 36 N 2 ): theoretical value C, 90.67; H, 5.27; N, 4.07; test value: C, 90.67; H, 5.28; N, 4.05. ESI-MS(m / z)(M + ): The theoretical value is 688.29, and the measured value is 688.65.

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Abstract

The invention discloses a compound containing spirodimethylanthrafluorene and its application in organic electroluminescent devices. The compound contains a spirodimethylanthrafluorene structure, has strong rigidity, and is connected to After the branched chain structure, it has the characteristics that it is not easy to crystallize and aggregate between molecules, and has good film-forming properties; the parent nucleus of the compound of the present invention has bipolarity, and the branched chain is an electron-donating group. Because the electron-donating ability of the group is different, Therefore, the HOMO energy level of the material is different, and can be used as a material for different functional layers; in addition, the compound of the present invention has a high triplet energy level, which can effectively block energy loss and facilitate energy transfer. Therefore, after the compound of the present invention is used as an organic electroluminescent functional layer material in an OLED device, the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved; at the same time, the device life is significantly improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing spirodimethylanthracene fluorene and its application in organic electroluminescent devices. 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, a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/80C07D209/86C07D209/88C07D209/94C07D405/12C07D471/04C07D487/04C07D491/048C07D491/052C07D491/056C07D491/147C07D491/153C07D495/04C07D498/04C07D498/14C07D513/04C09K11/06H01L51/54
CPCC09K11/06C07D209/80C07D209/86C07D209/88C07D209/94C07D405/12C07D471/04C07D487/04C07D491/048C07D491/052C07D491/056C07D491/147C07D491/153C07D495/04C07D498/04C07D498/14C07D513/04C09K2211/1092C09K2211/1088C09K2211/1029C09K2211/1011C09K2211/1037C09K2211/1033H10K85/624H10K85/636H10K85/6574H10K85/657H10K85/6572
Inventor 张兆超李崇王立春张小庆
Owner JIANGSU SUNERA TECH CO LTD
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