Compounds with 5H-dibenzo[a,d]cycloheptene as cores and application of compounds

A technology of dibenzocycloheptene and benzocycloheptene, which is applied in the preparation of amino compounds, the preparation of organic compounds, organic chemistry, etc., can solve different problems, maintain the stability of the film layer, improve the current efficiency and The effect of life and efficiency improvement

Active Publication Date: 2018-01-19
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 ha...

Method used

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  • Compounds with 5H-dibenzo[a,d]cycloheptene as cores and application of compounds
  • Compounds with 5H-dibenzo[a,d]cycloheptene as cores and application of compounds
  • Compounds with 5H-dibenzo[a,d]cycloheptene as cores and application of compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1: Intermediate B (i.e. H-R 1 , H-R 2 )Synthesis:

[0051]

[0052] Weigh raw material O and raw material P and dissolve 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 to 110 ° C for 10 to 24 hours, cool the reaction solution, filter the reaction solution, rotate the filtrate, and pass it through a silica gel column to obtain the target product; 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 to raw material O is 2.0~3.0:1;

[0053] Take the synthesis of intermediate B1 as an example:

[0054]

[0055] In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol aniline, 0.012mol bromobenzene, 150ml toluene, stir and...

Embodiment 2

[0060] Example 2: Synthesis of Intermediate AI and Intermediate AII:

[0061]

[0062] 250ml four-necked bottle, under nitrogen atmosphere, add 0.05mol Br-Ar 1 -Br and 1.2g of Mg powder (0.05mol), 60ml of tetrahydrofuran, heated to reflux for 4 hours, the reaction was complete, and Grignard reagent was generated; 10.3g of dibenzocyclohepten-5-one (0.05mol) was dissolved in 50mL of tetrahydrofuran, dropwise Add the above Grignard reagent, react at 60°C for 24 hours, a large amount of white Grignard salt precipitates, add saturated NHCl 4 The solution was until the precipitation disappeared, and the grit salt was converted into tertiary alcohol; after the reaction was completed, it was extracted with 100 ml of ether, the extract was dried with anhydrous sodium sulfate, and the solution was rotary evaporated to remove the solvent until no fraction was obtained to obtain a crude product of tertiary alcohol. The crude product of tertiary alcohol was The mixed solvent of petrole...

Embodiment 3

[0068] Example 3: Synthesis of Compound 2:

[0069]

[0070] In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol of Intermediate A2, 0.012mol of Intermediate B1, and 150ml of toluene, stir and mix, and 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 ℃, refluxed for 24 hours, sampling point plate, showed that no bromide remained, 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 98.8%, and the yield was 76.5%. Elemental analysis structure (molecular formula C 45 H 33 N): Theoretical C, 91.96; H, 5.66; N, 2.38; Tested C, 91.98; H, 5.65; N, 2.37. HPLC-MS: The molecular weight of the material is 587.77, and the measured molecular weight is 587.49.

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Abstract

The invention discloses compounds with 5H-dibenzo[a,d]cycloheptene as cores and an application of the compounds to OLED (organic light-emitting diode) devices. The compounds with 5H-dibenzo[a,d]cycloheptene as the cores are characterized in that central position of a heptyl ring of each compound is linked with a nitrogen-containing branch chain through phenyl, biphenyl or naphthyl. The compounds are not prone to crystallization and have good film forming property and heat stability as well as proper HOMO and LUMO energy level, by means of structure optimization of the devices, photoelectric property of the OLED devices can be improved effectively, and the service life of the OLED devices can be prolonged effectively.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound material containing dibenzocycloheptene as a central skeleton and its application in the field of OLED. Background technique [0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and new lighting products. 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 purpose 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, the positive and negative charges in the functional material film layer of the organic layer are acted by the electric field, and the positive and negative c...

Claims

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Application Information

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IPC IPC(8): C07C211/54C07C211/61C07D307/91C07D209/88C07D265/38C07D241/48C07D333/76C07D409/04C07D409/12C07D219/08C07D405/12C07C211/58C07D219/14C07C209/10C09K11/06H01L51/50H01L51/54
Inventor 吴秀芹李崇张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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