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Preparation method and purification method of 9,10-substituted anthracene

A catalyst and compound technology, which is applied in the field of preparation and purification of 9--10-phenyl)anthracene, can solve the problems of low product content and large impurities, and achieves high catalytic activity, few reaction impurities and fast main reaction speed. Effect

Inactive Publication Date: 2020-04-07
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to overcome the problems of large impurities and low product content in the existing methods, the present invention provides a synthesis and purification method of anthracene compounds substituted at 9 and 10 positions of the main material of blue light, which has high synthesis yield and the process is suitable for industrial production and other advantages

Method used

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  • Preparation method and purification method of 9,10-substituted anthracene
  • Preparation method and purification method of 9,10-substituted anthracene
  • Preparation method and purification method of 9,10-substituted anthracene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] A preparation method of anthracene substituted at 9,10 positions, specifically comprising the following steps:

[0046] The preparation of step 1, (2-(4-bromophenyl)naphthalene)

[0047]

[0048] Under argon protection, in a 300mL three-neck flask connected with a mechanical stirrer, a condenser, and a thermometer, add 2-naphthylboronic acid (30.0g), p-bromoiodobenzene (49.35g), Pd(PPh3) (4.60g), Potassium carbonate (24.11g), dioxane (150ml), water (60ml), reflux at 84-88°C for 9h, cool down to room temperature, filter, wash the filter cake with water until neutral (pH=7 ), after adding the reflux of 250ml toluene in the filter cake to divide water, cross the insulation column, cross the column liquid recrystallization, dry, obtain light yellow solid 2-(4-bromophenyl) naphthalene (being intermediate 1) 45.0g, The yield is 91.11%; LC-MS=283;

[0049] The preparation of step 2, 9-(1-naphthyl-) anthracene

[0050]

[0051] Under the protection of argon, into a 1L ...

Embodiment 2

[0066] The difference from Example 1 is that step 5 and the purification method in the preparation process are different, specifically:

[0067] Under the protection of argon, into a 500mL three-necked flask equipped with a mechanical stirrer, a condenser, and a thermometer, sequentially add (10-(1-naphthyl)anthracene-9-)boronic acid (10.0g), 2-(4-bromo Phenyl) naphthalene anthracene (18.31g), toluene (300ml), Pd-132 (0.020g), continue to heat up to 70 ° C ~ 76 ° C, continue to drop K 3 PO 4 Aqueous solution (K 3 PO 4 The aqueous solution consists of 58.28g K 3 PO 4 Mix it with 25ml of secondary ultrapure water) (continue dropwise for 2h), after the dropwise addition, reflux at 70°C to 76°C for 2h, cool the resulting reflux to 5°C to 20°C, filter, and wash the filter cake with water To neutral (pH=7), dry to constant weight at -0.08MPa~-0.09MPa, 70~80°C to obtain 12.95g of crude anthracene substituted at positions 9 and 10, the yield is 93.25%, and the HPLC purity is 99....

Embodiment 3

[0073] The difference from the above examples is that step 5 and the purification method in the preparation process are different, specifically:

[0074] Under the protection of argon, into a 500mL three-necked flask equipped with a mechanical stirrer, a condenser, and a thermometer, sequentially add (10-(1-naphthyl)anthracene-9-)boronic acid (10.0g), 2-(4-bromo Phenyl) naphthalene anthracene (18.31g), tetrahydrofuran (300ml), Pd-132 (0.020g), continue to heat up to 70 ° C ~ 76 ° C, continue to drop Cs 2 CO 3 Aqueous solution (Cs 2 CO 3 The aqueous solution consists of 89.37g Cs 2 CO 3 and 25ml of secondary ultrapure water) (continuously dropwise for 2h), after the dropwise addition, reflux at 70°C to 76°C for 2h, cool down to 5°C to 20°C, filter, and wash the filter cake to neutrality (pH = 7), dried to constant weight at -0.08MPa~-0.09MPa, 70~80°C to obtain 13.10 g of crude product of anthracene substituted at positions 9 and 10, with a yield of 93.85% and an HPLC purit...

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Abstract

The invention belongs to the technical field of organic synthesis and catalysis, and particularly relates to a preparation method for synthesizing 9-(naphthalene-1-yl)-10-(4-(naphthalene-2-yl)phenyl)anthracene through a five-step reaction, and a purification method. The method provided by the invention has the advantages of less catalyst dosage, high synthesis yield, less reaction by-products (impurities) (the content of removed boric acid products is less than 1%, and boric acid self-coupling products are not generated), high product purity (the HPLC purity is greater than or equal to 99.99%)and the like, and can be directly applied to OLED terminal materials of devices, and is simple, easy to operate and suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and catalysis, in particular to the preparation and purification of 9-(naphthalene-1-yl)-10-(4-(naphthalene-2-yl)phenyl)anthracene substituted at positions 9 and 10 method. Background technique [0002] Organic Light Emitting Diode (OLED) is the third-generation flat panel display following the cathode ray tube flat panel display and liquid crystal display. It has the advantages of active light emission, low driving voltage, high luminous brightness, fast response, and no X-ray pollution. The future mainstream display technology in the field. The luminous performance of OLED mainly depends on the OLED material. Therefore, in the preparation process of OLED materials, high-purity OLED materials and their intermediates are required. However, blue fluorescent materials have low color purity, and it is difficult to obtain dark blue with high color purity, and there is a problem that the sh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/32C07C7/00C07C7/14C07C15/28
CPCC07C1/321C07C17/263C07C17/12C07F5/025C07C7/005C07C7/14C07C15/28C07C25/22
Inventor 吴静杨伟博席敏毛涛王小伟
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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