Organic light emitting diode (OLED) intermediate 11-chlorine-7H-benzo[c]carbazole and synthesis method thereof

A synthesis method and intermediate technology are applied in the field of OLED intermediate 11-chloro-7H-benzo[c]carbazole and its synthesis, which can solve the problems of narrow viewing angle, low resolution, large power consumption and the like, Achieve the effects of high product yield and purity, wide application prospects, and reduced preparation costs

Active Publication Date: 2019-06-11
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002]With the advancement of the information industry, traditional displays can no longer meet people's requirements, such as cathode ray tube (CRT) displays with large volume and high driving voltage ; Liquid crystal display (LCD) has low brightness, narrow viewing angle, and small operating temperature range; plasma display panel (PDP) is expensive, has low resolution, and consumes a lot of power

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  • Organic light emitting diode (OLED) intermediate 11-chlorine-7H-benzo[c]carbazole and synthesis method thereof
  • Organic light emitting diode (OLED) intermediate 11-chlorine-7H-benzo[c]carbazole and synthesis method thereof
  • Organic light emitting diode (OLED) intermediate 11-chlorine-7H-benzo[c]carbazole and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0033] The synthetic method of 11-chloro-7H-benzo[c]carbazole specifically includes the following steps:

[0034] Step 1. Preparation of 1-(2-chloro-6-nitrophenyl)-naphthalene

[0035] Under a mechanical stirring speed of 200r / min, add 19.2g of 2,3-dichloronitrobenzene, 17.2g of 1-naphthaleneboronic acid, 63.6g of potassium phosphate, and 1.2g of Pd(0) into 192mL of ethanol After stirring evenly, react at 78℃ for 9h. After the reaction is complete, cool to room temperature, then add 192ml of water to the reaction solution, and then extract once with 192ml of toluene. After the extraction is completed, the organic phase is concentrated to obtain a concentrated solid. Recrystallization from ethanol yields 17.3 g of 1-(2-chloro-6-nitrophenyl)-naphthalene;

[0036] In this step, the yield of 1-(2-chloro-6-nitrophenyl)-naphthalene was 61.1%; the purity was 99.1%.

[0037] Step 2. Prepare 11-chloro-7H-benzo[c]carbazole

[0038] Under a mechanical stirring speed of 200r / min, 17.3g of 1-(2-ch...

Embodiment 2

[0043] The synthetic method of 11-chloro-7H-benzo[c]carbazole specifically includes the following steps:

[0044] Step 1. Preparation of 1-(2-chloro-6-nitrophenyl)-naphthalene

[0045] Under the mechanical stirring speed of 200r / min, add 19.2g of 2,3-dichloronitrobenzene, 17.2g of 1-naphthaleneboronic acid, 55.2g of potassium carbonate, and 0.6g of Pd(0) into 96ml of toluene After stirring uniformly, react at 78℃ for 9h. After the reaction is completed, cool to room temperature, then add 192ml of water to the reaction solution, and then extract once with 192ml of toluene to obtain an organic phase. Concentrate the organic phase to obtain a concentrated solid. Use 192ml for concentrated solids. Recrystallization from ethanol yields 12.5g of 1-(2-chloro-6-nitrophenyl)-naphthalene;

[0046] In this step, the yield of 1-(2-chloro-6-nitrophenyl)-naphthalene was 54.3%; the purity was 95.7%.

[0047] Step 2. Prepare 11-chloro-7H-benzo[c]carbazole

[0048] Under the mechanical stirring speed ...

Embodiment 3

[0050] The synthetic method of 11-chloro-7H-benzo[c]carbazole specifically includes the following steps:

[0051] Step 1. Preparation of 1-(2-chloro-6-nitrophenyl)-naphthalene

[0052] Under a mechanical stirring speed of 200r / min, 19.2g of 2,3-dichloronitrobenzene, 17.2g of 1-naphthaleneboronic acid, 21.2g of sodium carbonate, 2.4g of Pd(0) were added to 384ml of dioxygen In the six rings, stir well and react at 78°C for 6 hours. After the reaction is complete, cool to room temperature, then add the reaction solution to 192ml of water, and then extract with 192ml of toluene once to obtain an organic phase. Concentrate the organic phase to obtain a concentrated solid. Recrystallize with 192ml of ethanol to obtain 14.6g of 1-(2-chloro-6-nitrophenyl)-naphthalene;

[0053] In this step, the yield of 1-(2-chloro-6-nitrophenyl)-naphthalene is 51.7%; the purity is 94.8%.

[0054] Step 2. Prepare 11-chloro-7H-benzo[c]carbazole

[0055] Under the mechanical stirring speed of 200r / min, 14.6g o...

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Abstract

The invention discloses an organic light emitting diode (OLED) intermediate 11-chlorine-7H-benzo[c]carbazole and a synthesis method thereof. The specific synthesis steps are as follows: step 1, synthesizing 1-(2-chloro-6-nitrophenyl)-naphthalene: carrying out a Suzuki reaction on 2,3-dichloronitrobenzene with 1-naphthaleneboronic acid under an alkaline condition to synthesize the 1-(2-chloro-6-nitrophenyl)-naphthalene; step 2, synthesizing the 11-chlorine-7H-benzo[c]carbazole: carrying out reduction cyclization on the 1-(2-chloro-6-nitrophenyl)-naphthalene with triphenylphosphine to obtain the11-chlorine-7H-benzo[c]carbazole. The compound prepared by the method is an important OLED intermediate, the synthesis method disclosed by the invention is simple to operate, and the prepared productis relatively high in yield and purity, is suitable for industrial production, and has a wide application prospect.

Description

Technical field [0001] The invention belongs to the technical field of OLED intermediate materials, and specifically relates to an OLED intermediate 11-chloro-7H-benzo[c]carbazole and a synthesis method thereof. Background technique [0002] With the advancement of the information industry, traditional displays can no longer meet people's requirements. For example, cathode ray tube (CRT) displays are large in size and high in driving voltage; liquid crystal displays (LCD) have low brightness, narrow viewing angles, and The operating temperature range is small; the plasma display panel (PDP) is expensive, low resolution, and high power consumption. [0003] OLED (Organic Light Emitting Diode) has the advantages of being thin and light, active light emission, wide viewing angle, fast response, low energy consumption, excellent low temperature and shock resistance, and potential flexible design. The main reason is that OLED is an all-solid-state device without a vacuum cavity. No liq...

Claims

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Application Information

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Patent Type & AuthorityApplications(China)
IPC IPC(8): C07D209/80
CPCY02E10/549
Inventor王鹏飞李启贵张洋何晓芸霍东升胡华院徐亦为高仁孝
OwnerXIAN RUILIAN NEW MATERIAL CO LTD