CN109867619B - OLED intermediate 11-chloro-7H-benzo [ c ] carbazole and synthetic method thereof - Google Patents
OLED intermediate 11-chloro-7H-benzo [ c ] carbazole and synthetic method thereof Download PDFInfo
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Abstract
The invention discloses an OLED intermediate 11-chloro-7H-benzo [ c ] carbazole and a synthesis method thereof, and the synthesis method comprises the following steps: step 1, synthesis of 1- (2-chloro-6-nitrophenyl) -naphthalene: 2,3-dichloronitrobenzene and 1-naphthalene boric acid are synthesized into 1- (2-chloro-6-nitrophenyl) -naphthalene through a Suzuki reaction under an alkaline condition; step 2, synthesizing 11-chloro-7H-benzo [ c ] carbazole: the 1- (2-chlorine-6-nitrophenyl) -naphthalene and triphenylphosphine are subjected to reduction and cyclization to obtain 11-chlorine-7H-benzo [ c ] carbazole. The compound prepared by the invention is an important OLED intermediate, the synthesis method is simple to operate, and the prepared product has high yield and purity, is suitable for industrial production and has wide application prospect.
Description
Technical Field
The invention belongs to the technical field of OLED intermediate materials, and particularly relates to an OLED intermediate 11-chloro-7H-benzo [ c ] carbazole and a synthesis method thereof.
Background
With the progress of the information industry, the conventional display devices have failed to meet the requirements of people, such as the Cathode Ray Tube (CRT) display devices, which have large volume and high driving voltage; a Liquid Crystal Display (LCD) has low brightness, a narrow viewing angle and a small working temperature range; plasma Display Panels (PDPs) are expensive, have low resolution, and consume a lot of power.
The OLED (organic light emitting diode) has the advantages of thinness, lightness, active light emitting, wide visual angle, quick response, low energy consumption, excellent low temperature and anti-seismic performance, potential flexible design and the like, is mainly characterized in that the OLED is an all-solid-state device, has no vacuum cavity and liquid components, is not afraid of vibration, is convenient to use, has the characteristics of high resolution, wide visual angle, wide working temperature range and the like, and can be widely applied to the fields of weaponry and severe environment. In addition, the OLED can be used as a plane backlight source and an illumination light source in the display field. Therefore, the OLED has good development prospect. Therefore, it is necessary to increase the development of new OLED intermediates to broaden the application range of OLEDs.
Disclosure of Invention
The invention provides a novel OLED intermediate 11-chloro-7H-benzo [ c ] carbazole and a synthesis method thereof, the method comprises the steps of firstly enabling 2,3-dichloronitrobenzene and 1-naphthalene boric acid to react and synthesize 1- (2-chloro-6-nitrophenyl) -naphthalene through Suzuki reaction under the alkaline condition, and then utilizing 1- (2-chloro-6-nitrophenyl) -naphthalene and triphenylphosphine to reduce and cyclize to obtain 11-chloro-7H-benzo [ c ] carbazole.
The first purpose of the invention is to provide an OLED intermediate 11-chloro-7H-benzo [ c ] carbazole, which has the following specific structural formula:
the second purpose of the invention is to provide a synthetic method of 11-chloro-7H-benzo [ c ] carbazole, the synthetic route is as follows:
the synthesis steps are as follows:
step 1, synthesizing 1- (2-chloro-6-nitrophenyl) -naphthalene
2,3-dichloronitrobenzene and 1-naphthalene boric acid are synthesized into 1- (2-chloro-6-nitrophenyl) -naphthalene through a Suzuki reaction under an alkaline condition;
step 2, synthesizing 11-chloro-7H-benzo [ c ] carbazole
The 1- (2-chlorine-6-nitrophenyl) -naphthalene and triphenylphosphine are subjected to reduction and cyclization to obtain 11-chlorine-7H-benzo [ c ] carbazole.
Preferably, the specific steps for synthesizing 1- (2-chloro-6-nitrophenyl) -naphthalene in step 1 are as follows:
under the condition of stirring, adding 2,3-dichloronitrobenzene, 1-naphthalene boric acid, alkaline salt and zero-valent palladium Pd (0) into a first organic solvent, uniformly stirring, reacting at 60-78 ℃ for 6-15h, cooling to room temperature after the reaction is finished, and then extracting, concentrating and recrystallizing the reaction solution to obtain 1- (2-chloro-6-nitrophenyl) -naphthalene;
wherein, the molar ratio of 2,3-dichloronitrobenzene to 1-naphthalene boric acid to alkaline salt to zero-valent palladium is 1:1:1-4:0.005-0.02; 5363 and the dosage ratio of the 2,3-dichloronitrobenzene to the first organic solvent is 1g:5-20mL.
Preferably, the specific steps for synthesizing 11-chloro-7H-benzo [ c ] carbazole in step 2 are as follows:
under the condition of stirring, adding the 1- (2-chloro-6-nitrophenyl) -naphthalene prepared in the step 1 and triphenylphosphine into a second organic solvent, reacting at the temperature of 150-240 ℃ for 0.5-2H, evaporating the second organic solvent after the reaction is finished, and then recrystallizing to obtain 11-chloro-7H-benzo [ c ] carbazole;
wherein the mol ratio of the 1- (2-chloro-6-nitrophenyl) -naphthalene to the triphenylphosphine is 1:2-3; the dosage ratio of 1- (2-chloro-6-nitrophenyl) -naphthalene to high-boiling organic solvent is 1g:5-10mL.
Preferably, the alkaline salt is one of potassium phosphate, potassium carbonate, sodium carbonate and sodium bicarbonate.
Preferably, the first organic solvent is one of toluene, dioxane, DMF and ethanol.
Preferably, the second organic solvent is 1,2-dichlorobenzene or diphenyl ether.
Compared with the prior art, the invention has the beneficial effects that:
the invention takes 2,3-dichloronitrobenzene and 1-naphthalene boric acid as raw materials, under the alkaline condition, 1- (2-chlorine-6-nitrophenyl) -naphthalene is synthesized through Suzuki reaction, and the OLED intermediate 11-chlorine-7H-benzo [ c ] carbazole is obtained through triphenylphosphine reduction and cyclization of 1- (2-chlorine-6-nitrophenyl) -naphthalene. The method disclosed by the invention is simple to operate, high in product yield and purity, capable of reducing the preparation cost of the OLED material, suitable for industrial production and wide in application prospect.
Drawings
FIG. 1 is a MS spectrum of 11-chloro-7H-benzo [ c ] carbazole prepared in example 1 of the present invention.
Detailed Description
In order to make the technical solutions of the present invention better understood and enable one skilled in the art to practice the present invention, the present invention is further described below with reference to specific examples and drawings, but the examples are not intended to limit the present invention.
In the present invention, 11-chloro-7H-benzo [ c ] carbazole has the following structural formula:
the specific synthetic route of 11-chloro-7H-benzo [ c ] carbazole is as follows:
the experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
The synthesis method of 11-chloro-7H-benzo [ c ] carbazole specifically comprises the following steps:
step 1, preparation of 1- (2-chloro-6-nitrophenyl) -naphthalene
Under the mechanical stirring speed of 200r/min, adding 19.2g of 2,3-dichloronitrobenzene, 17.2g of 1-naphthalene boric acid, 63.6g of potassium phosphate and 1.2g of Pd (0) into 192mL of ethanol, uniformly stirring, reacting at 78 ℃ for 9h, cooling to room temperature after the reaction is finished, adding 192mL of water into the reaction liquid, extracting once with 192mL of toluene, concentrating the organic phase after the extraction is finished to obtain concentrated solid, and recrystallizing the concentrated solid with 192mL of ethanol to obtain 17.3g of 1- (2-chloro-6-nitrophenyl) -naphthalene;
in this step, the yield of 1- (2-chloro-6-nitrophenyl) -naphthalene is 61.1%; the purity was 99.1%.
Step 2, preparing 11-chloro-7H-benzo [ c ] carbazole
Under the mechanical stirring speed of 200r/min, adding 17.3g of 1- (2-chloro-6-nitrophenyl) -naphthalene and 32.0g of triphenylphosphine into 173ml of 1,2-dichlorobenzene, reacting for 2H at 180 ℃, evaporating 1,2-dichlorobenzene after the reaction is finished, and then recrystallizing with 86.5ml of toluene to obtain 10.0g of 11-chloro-7H-benzo [ c ] carbazole;
in the step, the yield of the obtained 11-chloro-7H-benzo [ c ] carbazole is 65.3%; the purity was 93.6%.
The structural characterization data for the product is: 1 H-NMR(400MHz,CDCl 3 ,TMS):δ(ppm)11.66(s，1H)，8.54(d,J＝7.2Hz,1H)，7.99(d,J＝7.2Hz,1H)，7.65(d,J＝8.4Hz,1H)，7.61(m,1H)，7.58(d,J＝8.4Hz,1H),7.53(m,1H)，7.51(d,J＝8.4Hz,1H),7.31(m,1H)，7.01(d,J＝8.4Hz,1H)；
11-chloro-7H-benzo [ c ] prepared in example 1]The mass spectrum of carbazole is shown in FIG. 1, APCI-MS M/z (rel. Int.): calcd 251.7found 250.6 (M) - )。
Example 2
The synthesis method of 11-chloro-7H-benzo [ c ] carbazole specifically comprises the following steps:
step 1, preparation of 1- (2-chloro-6-nitrophenyl) -naphthalene
Under the mechanical stirring speed of 200r/min, 19.2g of 2,3-dichloronitrobenzene, 17.2g of 1-naphthalene boric acid, 55.2g of potassium carbonate and 0.6g of Pd (0) are added into 96ml of toluene, the mixture is uniformly stirred and then reacts at 78 ℃ for 9 hours, after the reaction is finished, the mixture is cooled to room temperature, 192ml of water is added into the reaction liquid, 192ml of toluene is used for extraction once to obtain an organic phase, the organic phase is concentrated to obtain a concentrated solid, and the concentrated solid is recrystallized by 192ml of ethanol to obtain 12.5g of 1- (2-chloro-6-nitrophenyl) -naphthalene;
in this step, the yield of 1- (2-chloro-6-nitrophenyl) -naphthalene is 54.3%; the purity was 95.7%.
Step 2, preparation of 11-chloro-7H-benzo [ c ] carbazole
Under the mechanical stirring speed of 200r/min, 12.5g of 1- (2-chloro-6-nitrophenyl) -naphthalene and 28.9g of triphenylphosphine are added into 125mL of diphenyl ether, the mixture reacts for 2H at 200 ℃, after the reaction is finished, the diphenyl ether is evaporated, and then the mixture is recrystallized by 62.5mL of toluene, thus obtaining 8.2g of 11-chloro-7H-benzo [ c ] carbazole; the yield of the obtained 11-chloro-7H-benzo [ c ] carbazole is 73.7%; the purity was 94.3%.
Example 3
The synthesis method of 11-chloro-7H-benzo [ c ] carbazole specifically comprises the following steps:
step 1, preparation of 1- (2-chloro-6-nitrophenyl) -naphthalene
Under the mechanical stirring speed of 200r/min, adding 19.2g of 2,3-dichloronitrobenzene, 17.2g of 1-naphthalene boric acid, 21.2g of sodium carbonate and 2.4g of Pd (0) into 384ml of dioxane, uniformly stirring, reacting at 78 ℃ for 6h, cooling to room temperature after the reaction is finished, adding the reaction liquid into 192ml of water, extracting once with 192ml of toluene to obtain an organic phase, concentrating the organic phase to obtain a concentrated solid, and recrystallizing the concentrated solid with 192ml of ethanol to obtain 14.6g of 1- (2-chloro-6-nitrophenyl) -naphthalene;
in this step, the yield of 1- (2-chloro-6-nitrophenyl) -naphthalene was 51.7%; the purity was 94.8%.
Step 2, preparing 11-chloro-7H-benzo [ c ] carbazole
Under the mechanical stirring speed of 200r/min, 14.6g of 1- (2-chloro-6-nitrophenyl) -naphthalene and 40.5g of triphenylphosphine are added into 146mL of diphenyl ether, the mixture reacts for 2 hours at 240 ℃, the solvent diphenyl ether is evaporated after the reaction is finished, and then 73mL of toluene is used for recrystallization, so that 8.9g of 11-chloro-7H-benzo [ c ] carbazole is obtained; the yield of the obtained 11-chloro-7H-benzo [ c ] carbazole is 68.9%; the purity was 95.7%.
Example 4
The synthesis method of 11-chloro-7H-benzo [ c ] carbazole specifically comprises the following steps:
step 1, preparation of 1- (2-chloro-6-nitrophenyl) -naphthalene
Under the mechanical stirring speed of 200r/min, 19.2g of 2,3-dichloronitrobenzene, 17.2g of 1-naphthalene boric acid, 8.4g of sodium bicarbonate and 0.6g of Pd (0) are added into 288ml of DMF, the mixture is uniformly stirred and then reacts at 60 ℃ for 15h, the reaction solution is cooled to room temperature after the reaction is finished, then the reaction solution is added into 192ml of water and extracted once by 192ml of toluene to obtain an organic phase, the organic phase is concentrated to obtain a concentrated solid, and the concentrated solid is recrystallized by 192ml of ethanol to obtain 13.7g of 1- (2-chloro-6-nitrophenyl) -naphthalene;
in the step, the yield of the 1- (2-chloro-6-nitrophenyl) -naphthalene is 48.3%; the purity was 94.3%.
Step 2, preparing 11-chloro-7H-benzo [ c ] carbazole
Adding 13.7g of 1- (2-chloro-6-nitrophenyl) -naphthalene and 31.7g of triphenylphosphine into 68.5ml of 1,2-dichlorobenzene at a mechanical stirring speed of 200r/min, reacting for 0.5H at 150 ℃, evaporating a solvent 1,2-dichlorobenzene after the reaction is finished, and recrystallizing by using 68.5ml of toluene to obtain 5.0g of 11-chloro-7H-benzo [ c ] carbazole; the yield of the obtained 11-chloro-7H-benzo [ c ] carbazole is 51.3%; the purity was 94.8%.
While the present invention has been described with respect to preferred embodiments, additional variations and modifications will occur to those embodiments once the basic inventive concepts are known to those skilled in the art. Therefore, it is intended that the appended claims be interpreted as including preferred embodiments and all such alterations and modifications as fall within the scope of the invention.
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, it is intended that such changes and modifications be included within the scope of the appended claims and their equivalents.
Claims (4)
1. A method for synthesizing an OLED intermediate 11-chloro-7H-benzo [ c ] carbazole is characterized in that the structural formula of the 11-chloro-7H-benzo [ c ] carbazole is as follows:
and the synthetic route is as follows:
the synthesis steps are as follows:
step 1, synthesis of 1- (2-chloro-6-nitrophenyl) -naphthalene
2,3-dichloronitrobenzene and 1-naphthalene boric acid are synthesized into 1- (2-chloro-6-nitrophenyl) -naphthalene through a Suzuki reaction under an alkaline condition;
step 2, synthesizing 11-chloro-7H-benzo [ c ] carbazole
Reducing and cyclizing 1- (2-chlorine-6-nitrophenyl) -naphthalene and triphenylphosphine to obtain 11-chlorine-7H-benzo [ c ] carbazole;
the specific steps for synthesizing 11-chloro-7H-benzo [ c ] carbazole in step 2 are as follows:
under the condition of stirring, adding the 1- (2-chloro-6-nitrophenyl) -naphthalene prepared in the step 1 and triphenylphosphine into a second organic solvent, reacting at the temperature of 150-240 ℃ for 0.5-2H, evaporating the second organic solvent after the reaction is finished, and then recrystallizing to obtain 11-chloro-7H-benzo [ c ] carbazole;
wherein the mol ratio of the 1- (2-chloro-6-nitrophenyl) -naphthalene to the triphenylphosphine is 1:2-3; the dosage ratio of the 1- (2-chloro-6-nitrophenyl) -naphthalene to the second organic solvent is 1g:5-10mL;
in the step 2, the second organic solvent is 1,2-dichlorobenzene or diphenyl ether.
2. The method for synthesizing 11-chloro-7H-benzo [ c ] carbazole according to claim 1, wherein the specific steps for synthesizing 1- (2-chloro-6-nitrophenyl) -naphthalene in step 1 are as follows:
under the condition of stirring, adding 2,3-dichloronitrobenzene, 1-naphthalene boric acid, alkaline salt and zero-valent palladium into a first organic solvent, uniformly stirring, reacting at 60-78 ℃ for 6-15h, cooling to room temperature after the reaction is finished, and then extracting, concentrating and recrystallizing the reaction solution to obtain 1- (2-chloro-6-nitrophenyl) -naphthalene;
wherein, the molar ratio of 2,3-dichloronitrobenzene to 1-naphthalene boric acid to alkaline salt to zero-valent palladium is 1:1:1-4:0.005-0.02;2,3-dichloronitrobenzene and the first organic solvent in a dosage ratio of 1g:5-20mL.
3. The method of synthesizing 11-chloro-7H-benzo [ c ] carbazole according to claim 2, wherein said basic salt is one of potassium phosphate, potassium carbonate, sodium bicarbonate.
4. The method of claim 2, wherein the first organic solvent is one of toluene, dioxane, DMF, and ethanol.
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