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A kind of organic compound containing spirodibenzocycloheptenene fluorene and its application

A technology of benzocycloheptene fluorene and organic compounds, which is applied in the preparation of organic compounds, organic chemistry, preparation of amino compounds, etc., can solve problems such as differences

Active Publication Date: 2020-12-18
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 kind of organic compound containing spirodibenzocycloheptenene fluorene and its application
  • A kind of organic compound containing spirodibenzocycloheptenene fluorene and its application
  • A kind of organic compound containing spirodibenzocycloheptenene fluorene and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the synthesis of intermediate BI:

[0054]

[0055] Weigh raw material O and raw material P and dissolve them with toluene, then add Pd 2 (dba) 3 , P(Ph) 3 and sodium tert-butoxide; under an inert atmosphere, react the mixed solution of the above reactants at a reaction temperature of 90-110°C for 10-24 hours, cool and filter the reaction solution, spin the filtrate, and pass through a silica gel column to obtain the intermediate BI ; The molar ratio of the raw material O to the raw material P is 1:(1.0~1.5); Pd 2 (dba) 3 The molar ratio to raw material O is (0.006~0.02):1, and the molar ratio of sodium tert-butoxide to raw material P is (2.0~3.0):1; P(Ph) 3 The molar ratio with raw material O is (2.0~3.0):1;

[0056] Take the synthesis of intermediate B1 as an example:

[0057]

[0058] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material O1, 0.012mol raw material P1, 150ml toluene and stir to mix, then add 5...

Embodiment 2

[0059] Embodiment 2: the synthesis of intermediate BII:

[0060]

[0061] The concrete preparation method of above-mentioned reaction is: take intermediate BI and raw material N, dissolve with toluene; Add Pd 2 (dba) 3 , P(Ph) 3 , sodium tert-butoxide; under an inert atmosphere, react the mixed solution of the above-mentioned reactants at 95-110° C. for 10-24 hours, cool and filter the reaction solution, spin the filtrate, and pass through a silica gel column to obtain intermediate C; The molar ratio of the intermediate BI to the raw material N is 1:(1.0~1.5), Pd 2 (dba) 3 The molar ratio to the intermediate BI is (0.006~0.02):1, P(Ph) 3 The molar ratio of sodium tert-butoxide to intermediate BI is (0.006-0.02):1, and the molar ratio of sodium tert-butoxide to intermediate BI is (1.0-3.0):1.

[0062] Under nitrogen atmosphere, weigh intermediate C, bis(pinacolate) diboron, Pd(dppf)Cl 2 1. Potassium acetate was dissolved in toluene, reacted at 100-120°C for 12-24 hours...

Embodiment 3

[0070] Embodiment 3: the synthesis of intermediate AI:

[0071]

[0072] In an oven-dried flask, 0.01 mol of raw material N was dissolved in 500 mL of anhydrous THF, and the reaction mixture was cooled to -78°C, then, 34.3 mL of n-BuLi (2.5 mol / L, hexane solution), stirred for 1 h, then 0.01 mol of starting material M was dissolved in THF and added dropwise at -70°C. After the addition was complete, the reaction mixture was gradually warmed to room temperature, extracted with ammonium chloride and concentrated on a rotary evaporator, 500 mL of acetic acid was carefully added to the concentrated solution, followed by 100 mL of fuming hydrochloric acid. The mixture was heated to 75 °C for 5 h during which a white solid came out, then the mixture was cooled to room temperature and the precipitated solid was filtered off with suction, washed with methanol and the residue was dried at 40 °C under reduced pressure.

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Abstract

The invention discloses an organic compound containing spirofluorene dibenzocycloheptene and an application of the organic compound. The compound with spirofluorene dibenzocycloheptene as a core is connected with a nitrogen-containing branched chain through phenyl, biphenyl or naphthyl. The compound is not prone to crystallization, has good film-forming property and heat stability and has higher glass transition temperature and proper HOMO and LUMO energy levels; by means of optimization of device structure, photoelectric property of an OLED (organic light emission diode) device can be effectively improved, and the service life of the OLED device can be effectively prolonged, so that application requirements of a panel manufacturing enterprise can be met better.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound material with spirodibenzocycloheptenene fluorene as the central skeleton and its application in the field of OLEDs. 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-emit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/61C07C209/10C07D307/91C07D219/14C07D241/48C07D265/38C07D333/76H01L51/50H01L51/54
Inventor 王立春吴秀芹张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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