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Compound using spirobibenzocycloheptene fluorene as core, and applications in organic electroluminescent devices

A technology of benzocycloheptene fluorene and compound, applied in the application field of organic electroluminescence devices, can solve problems such as disparity

Inactive Publication Date: 2020-01-07
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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  • Compound using spirobibenzocycloheptene fluorene as core, and applications in organic electroluminescent devices
  • Compound using spirobibenzocycloheptene fluorene as core, and applications in organic electroluminescent devices
  • Compound using spirobibenzocycloheptene fluorene as core, and applications in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Embodiment 1: the synthesis of intermediate AI:

[0082]

[0083] (1) Weigh the raw material H1 and dissolve it in tetrahydrofuran, then add the raw material L1, react the above reactant mixed solution at 60°C for 24 hours, add saturated NHCl 4 Grignard salt is converted into alcohol; after the reaction is completed, ether extraction, drying and rotary evaporation, petroleum ether: dichloromethane mixed solvent (3:2) silica gel column purification to obtain intermediate F1; the molar ratio of the raw material H1 to the raw material L1 It is 1:1.0~1.5.

[0084] (2) Weigh intermediate F1, dissolve it with dichloromethane, add boron trifluoride etherate complex dropwise at room temperature, react for 30 minutes, add ethanol and water to quench the reaction, extract with dichloromethane, dry and spin Steam, petroleum ether silica gel column purification, recrystallization with ethanol: dichloromethane (volume ratio 1:1), obtain intermediate F2; The mol ratio of describe...

Embodiment 2

[0096] Embodiment 2: the synthesis of intermediate AII:

[0097]

[0098] (1) Under the protection of nitrogen, weigh the raw material H2, stir and dissolve it with tetrahydrofuran, add the raw material L2 dropwise, react at 60°C for 24 hours, a large amount of white precipitate is formed, and finally add saturated NHCl 4 Convert the Grignard salt into alcohol; after the reaction, extract with ether, dry and rotary evaporate, and purify on a silica gel column with a mixed solvent of petroleum ether: dichloromethane (3:2) to obtain a slightly yellow solid intermediate G1. The molar ratio of the raw material H2 to the raw material L1 is 1:1.0-1.5.

[0099] (2) Weigh intermediate G1, dissolve in dichloromethane, add boron trifluoride etherate complex dropwise at room temperature, react for 30 minutes, add ethanol and water to quench the reaction, extract with dichloromethane, dry and spin Evaporation, petroleum ether silica gel column purification, and recrystallization with ...

Embodiment 3

[0117] Embodiment 3: the synthesis of intermediate A15:

[0118]

[0119] (1) In a 500mL three-neck flask, under nitrogen protection, add 0.05mol raw material H3-1, 0.06mol raw material Q2-1, dissolve with a mixed solvent (180ml toluene, 90ml ethanol), and then add 0.15mol Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0005mol Pd(PPh 3 ) 4 , heating to reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain an intermediate M1-1 with a HPLC purity of 98.4% and a yield of 76.1%. Elemental analysis structure (molecular formula C 21 h 14 o 3 ): theoretical value C, 80.24; H, 4.49; 0, 15.27; test value: C, 80.24; H, 4.50; 0, 15.26. ESI-MS(m / z)(M + ): The theoretical value is 314.09, and the measured value is 314.02.

[0120] (2) In a 250mL three-necked flask, under the protection of nitrogen, add 0.03mol of inter...

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Abstract

The invention discloses a compound using spirobibenzocycloheptene fluorene as a core, and applications in organic electroluminescent devices. According to the invention, the compound contains aspirobibenzocycloheptene fluorene structure, has strong rigidity, and further has characteristics of difficult crystallization and aggregation among molecules, good film-forming property and the like after the compound is linked to a carbazole derivative long branched chain structure or an arylamine derivative branched chain structure; due to different electron donating capacities of the branched chain groups, the HOMO energy levels of the material are different, and the compound can be used as different functional layer materials; the compound has high triplet state energy level, can effectively block energy loss, and is beneficial to energy transfer; and with the application of the compound as the organic electroluminescent functional layer material in the OLED device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved while the service life of the device is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with spirodibenzocycloheptenene fluorene as its core and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can not only be used to manufacture new display products, but also can be used to make new lighting products, and is expected to replace the existing liquid crystal display and fluorescent lighting, and has a very wide application prospect . The OLED light-emitting device is 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 ligh...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07D491/048C07D307/91C07D405/12C07D307/77C07D495/04C07D471/04C07D471/14C07D491/147C07D495/14C07D221/18C07D413/04C07D405/04C07D405/10C07D498/04C07D491/056C07D265/34C07D279/14H01L51/50H01L51/54
CPCC07C211/61C07D491/048C07D307/91C07D405/12C07D307/77C07D495/04C07D471/04C07D471/14C07D491/147C07D495/14C07D221/18C07D413/04C07D405/04C07D405/10C07D498/04C07D491/056C07D265/34C07D279/14C07C2603/18C07C2603/94H10K85/626H10K85/633H10K85/657H10K85/6576H10K85/6574H10K85/6572H10K50/00
Inventor 李崇庞羽佳王芳张兆超
Owner JIANGSU SUNERA TECH CO LTD
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