CN109867619A - A kind of chloro- 7H- benzo [c] carbazole of OLED intermediate 11- and its synthetic method - Google Patents
A kind of chloro- 7H- benzo [c] carbazole of OLED intermediate 11- and its synthetic method Download PDFInfo
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Abstract
The invention discloses a kind of chloro- 7H- benzo [c] carbazole of OLED intermediate 11- and its synthetic methods, specific synthesis step is as follows: step 1, synthesis 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene: 2,3- dichloronitrobenzene and 1- naphthalene boronic acids react synthesis 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene under alkaline condition, by Suzuki；Step 2, synthesize chloro- 7H- benzo [c] carbazole of 11-: 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene and triphenylphosphine reduction cyclization obtain chloro- 7H- benzo [c] carbazole of 11-.The compound that the present invention prepares is important OLED intermediate, and synthetic method of the invention is easy to operate, and the yield and purity for the product prepared are higher, is suitable for industrial production, and have wide application prospect.
Description
Technical field
The invention belongs to OLED intermediary material technical fields, and in particular to a kind of chloro- 7H- benzo of OLED intermediate 11-
[c] carbazole and its synthetic method.
Background technique
With the progress of information industry, traditional display has been unable to meet the requirement of people, such as cathode-ray tube
(cathode ray tube, CRT) display volume is big, driving voltage is high；Liquid crystal display (liquid crystal
Display, LCD) brightness is low, narrow viewing angle, operating temperature range are small；Plasma display (plasma display panel,
PDP it) involves great expense, resolution ratio is not high, power consumption is big.
OLED (Organic Light Emitting Diode) is with thin and lightweight, active shines, wide viewing angle, quick response, low energy consumption, low temperature
With the advantages that anti-seismic performance is excellent and potential flexible design, essentially consisting in OLED is full solid-state device, no vacuum chamber, aneroid
State ingredient, it is easy to use so be not afraid of vibration, in addition high resolution, the features such as visual angle is wide and operating temperature range is wide, in weapon
Equipment and adverse circumstances field will be used widely.In addition, OLED is alternatively arranged as the planar backlight source and photograph of display field
Bright light source applications.It can be seen that OLED has good development prospect.Therefore, it is necessary to increase novel OLED intermediate
Exploitation dynamics, to widen the application range of OLED.
Summary of the invention
The present invention provides a kind of chloro- 7H- benzo [c] carbazole of novel OLED intermediate 11- and its synthetic method, this method
2,3- dichloronitrobenzene and 1- naphthalene boronic acids are allowed first under alkaline condition, and synthesis 1- (the chloro- 6- nitrobenzene of 2- is reacted by Suzuki
Base)-naphthalene, then chloro- 7H- benzo [c] click of 11- is obtained using 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene and triphenylphosphine reduction cyclization
Azoles.
The first purpose of the invention is to provide a kind of chloro- 7H- benzo [c] carbazole of OLED intermediate 11-, specific structures
Formula is as follows:
A second object of the present invention is to provide the synthetic method of chloro- 7H- benzo [c] carbazole of 11-, synthetic route is as follows:
Synthesis step is as follows:
Step 1,1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene is synthesized
2,3- dichloronitrobenzenes and 1- naphthalene boronic acids react synthesis 1- (the chloro- 6- nitro of 2- under alkaline condition, by Suzuki
Phenyl)-naphthalene；
Step 2, chloro- 7H- benzo [c] carbazole of 11- is synthesized
1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene and triphenylphosphine reduction cyclization obtain chloro- 7H- benzo [c] carbazole of 11-.
Preferably, specific step is as follows for-naphthalene for synthesis 1- (the chloro- 6- nitrobenzophenone of 2-) in step 1:
Under agitation, by 2,3- dichloronitrobenzene, 1- naphthalene boronic acids, basic salt, zeroth order palladium Pd (0) is added to first has
In solvent, 6-15h is reacted at 60-78 DEG C after mixing evenly, is cooled to room temperature after completion of the reaction, then extracts reaction solution
It takes, be concentrated, recrystallizing to get 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene；
Wherein, 2,3- dichloronitrobenzene, 1- naphthalene boronic acids, basic salt, zeroth order palladium molar ratio be 1:1:1-4:0.005-
0.02；The amount ratio of 2,3 dichloro nitro benzene and the first organic solvent is 1g:5-20mL.
Preferably, specific step is as follows for synthesis chloro- 7H- benzo [c] carbazole of 11- in step 2:
Under agitation, (the chloro- 6- nitrobenzophenone of the 2-)-naphthalene of 1- made from step 1 and triphenylphosphine are added to second
In organic solvent, 0.5-2h is reacted at 150-240 DEG C, steams the second organic solvent after completion of the reaction, then recrystallize to get
Chloro- 7H- benzo [c] carbazole of 11-；
Wherein, 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene, triphenylphosphine molar ratio be 1:2-3；1- (the chloro- 6- nitrobenzene of 2-
Base)-naphthalene and higher boiling it is organic] amount ratio of solvent is 1g:5-10mL.
Preferably, the basic salt is one of potassium phosphate, potassium carbonate, sodium carbonate, sodium bicarbonate.
Preferably, first organic solvent is one of toluene, dioxane, DMF, ethyl alcohol.
Preferably, second organic solvent is 1,2- dichloro-benzenes or diphenyl ether.
Compared with the conventional method, the beneficial effects of the present invention are:
The present invention, for raw material, under alkaline condition, is reacted by Suzuki and is closed with 2,3- dichloronitrobenzene and 1- naphthalene boronic acids
At 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene, 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene restores cyclization by triphenylphosphine and obtains in OLED
Chloro- 7H- benzo [c] carbazole of mesosome 11-.Method of the invention is easy to operate, and product yield and purity is high can reduce OLED material
The preparation cost of material is suitable for industrial production, has wide application prospect.
Detailed description of the invention
Fig. 1 is the MS map for chloro- 7H- benzo [c] carbazole of 11- that the embodiment of the present invention 1 is prepared.
Specific embodiment
In order to enable those skilled in the art to more fully understand, technical solution of the present invention is practiced, below with reference to specific
The invention will be further described for embodiment and attached drawing, but illustrated embodiment is not as a limitation of the invention.
In the present invention, the structural formula of chloro- 7H- benzo [c] carbazole of 11- is as follows:
The specific synthetic route of chloro- 7H- benzo [c] carbazole of 11- is as follows:
Experimental method described in following each embodiments is conventional method unless otherwise specified；The reagent and material, such as
Without specified otherwise, can be commercially available on the market.
Embodiment 1
The synthetic method of chloro- 7H- benzo [c] carbazole of 11-, specifically includes the following steps:
Step 1,1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene is prepared
Under the mechanical stirring speed of 200r/min, by 2, the 3- dichloronitrobenzene of 19.2g, 17.2g 1- naphthalene boronic acids,
The potassium phosphate of 63.6g, the Pd (0) of 1.2g are added in 192mL ethyl alcohol, react 9h, end of reaction at 78 DEG C after mixing evenly
After be cooled to room temperature, 192ml water is then added into reaction solution, then primary with the extraction of 192ml toluene, being concentrated after extraction has
Machine phase, obtains thickened solid, and thickened solid uses 192ml ethyl alcohol recrystallization to get 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene again
17.3g；
In this step, the yield of 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene is 61.1%；Purity is 99.1%.
Step 2, chloro- 7H- benzo [c] carbazole of 11- is prepared
Under the mechanical stirring speed of 200r/min, by 1- (the chloro- 6- nitrobenzophenone of the 2-)-naphthalene and 32.0g triphen of 17.3g
Base phosphine is added in 1, the 2- dichloro-benzenes of 173ml, and 2h is reacted at 180 DEG C, is steamed 1,2- dichloro-benzenes after completion of the reaction, is then used
86.5ml re crystallization from toluene is to get chloro- 7H- benzo [c] the carbazole 10.0g of 11-；
In this step, the yield of chloro- 7H- benzo [c] carbazole of obtained 11- is 65.3%；Purity is 93.6%.
The structural characterization data of product are as follows:1H-NMR(400MHz,CDCl3, 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)；
The mass spectrogram of chloro- 7H- benzo [c] carbazole of 11- made from embodiment 1 is shown in Fig. 1, APCI-MS m/z (rel.int.):
calcd 251.7found 250.6(M-)。
Embodiment 2
The synthetic method of chloro- 7H- benzo [c] carbazole of 11-, specifically includes the following steps:
Step 1,1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene is prepared
Under the mechanical stirring speed of 200r/min, by 2, the 3- dichloronitrobenzene of 19.2g, 17.2g 1- naphthalene boronic acids,
The potassium carbonate of 55.2g, the Pd (0) of 0.6g are added in 96ml toluene, react 9h at 78 DEG C after mixing evenly, after completion of the reaction
It is cooled to room temperature, 192ml water is then added into reaction solution, again with toluene 192ml extraction is primary, obtains organic phase, concentration has
Machine phase obtains thickened solid, and thickened solid is with 192ml ethyl alcohol recrystallization to get 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene 12.5g；
In this step, the yield of 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene is 54.3%；Purity is 95.7%.
Step 2, chloro- 7H- benzo [c] carbazole of 11- is prepared
Under the mechanical stirring speed of 200r/min, by 1- (the chloro- 6- nitrobenzophenone of the 2-)-naphthalene and 28.9g triphen of 12.5g
Base phosphine is added in 125mL diphenyl ether, and 2h is reacted at 200 DEG C, steams diphenyl ether after completion of the reaction, then uses 62.5ml toluene
Recrystallization is to get chloro- 7H- benzo [c] the carbazole 8.2g of 11-；The yield of chloro- 7H- benzo [c] carbazole of obtained 11- is 73.7%；
Purity is 94.3%.
Embodiment 3
The synthetic method of chloro- 7H- benzo [c] carbazole of 11-, specifically includes the following steps:
Step 1,1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene is prepared
Under the mechanical stirring speed of 200r/min, by 2, the 3- dichloronitrobenzene of 19.2g, 17.2g 1- naphthalene boronic acids,
The sodium carbonate of 21.2g, the Pd (0) of 2.4g are added in 384ml dioxane, react 6h at 78 DEG C after mixing evenly, reaction
After be cooled to room temperature, then by reaction solution be added 192ml water in, then with 192ml toluene extraction once, obtain organic phase,
Organic phase is concentrated, obtains thickened solid, thickened solid is with 192ml ethyl alcohol recrystallization to get 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene
14.6g；
In this step, the yield of 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene is 51.7%；Purity is 94.8%.
Step 2, chloro- 7H- benzo [c] carbazole of 11- is prepared
Under the mechanical stirring speed of 200r/min, by 1- (the chloro- 6- nitrobenzophenone of the 2-)-naphthalene and 40.5g triphen of 14.6g
Base phosphine is added in 146mL diphenyl ether, and 2h is reacted at 240 DEG C, steams solvent diphenyl ether after completion of the reaction, then uses 73ml first
Benzene recrystallizes to get chloro- 7H- benzo [c] the carbazole 8.9g of 11-；The yield of chloro- 7H- benzo [c] carbazole of obtained 11- is
68.9%；Purity is 95.7%.
Embodiment 4
The synthetic method of chloro- 7H- benzo [c] carbazole of 11-, specifically includes the following steps:
Step 1,1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene is prepared
Under the mechanical stirring speed of 200r/min, by 2, the 3- dichloronitrobenzene of 19.2g, 17.2g 1- naphthalene boronic acids,
The sodium bicarbonate of 8.4g, the Pd (0) of 0.6g are added in 288ml DMF, are reacted 15h at 60 DEG C after mixing evenly, have been reacted
It is cooled to room temperature after finishing, then reaction solution is added in 192ml water, extracted once with toluene 192ml, obtain organic phase, be concentrated
Organic phase obtains thickened solid, and thickened solid is with 192ml ethyl alcohol recrystallization to get 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene
13.7g；
In this step, the yield of 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene is 48.3%；Purity is 94.3%.
Step 2, chloro- 7H- benzo [c] carbazole of 11- is prepared
Under the mechanical stirring speed of 200r/min, by the three of 1- (the chloro- 6- nitrobenzophenone of the 2-)-naphthalene of 13.7g and 31.7g
Phenylphosphine is added in 1, the 2- dichloro-benzenes of 68.5ml, and 0.5h is reacted at 150 DEG C, steams solvent 1,2- dichloro after completion of the reaction
Benzene, then with 68.5ml re crystallization from toluene to get chloro- 7H- benzo [c] the carbazole 5.0g of 11-；The chloro- 7H- benzo [c] of obtained 11-
The yield of carbazole is 51.3%；Purity is 94.8%.
The present invention describes preferred embodiment, and once a person skilled in the art knows basic creative general
It reads, then additional changes and modifications can be made to these embodiments.So it includes preferred real that the following claims are intended to be interpreted as
It applies example and falls into all change and modification of the scope of the invention.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art
Mind and range.In this way, if these modifications and changes of the present invention belongs to the range of the claims in the present invention and its equivalent technologies
Within be also intended to include these modifications and variations.
Claims (7)
1. a kind of chloro- 7H- benzo [c] carbazole of OLED intermediate 11-, which is characterized in that structural formula is as follows:
2. the synthetic method of chloro- 7H- benzo [c] carbazole of 11- according to claim 1, which is characterized in that synthetic route is such as
Under:
Synthesis step is as follows:
Step 1,1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene is synthesized
2,3- dichloronitrobenzenes and 1- naphthalene boronic acids react synthesis 1- (the chloro- 6- nitrobenzene of 2- under alkaline condition, by Suzuki
Base)-naphthalene；
Step 2, chloro- 7H- benzo [c] carbazole of 11- is synthesized
1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene and triphenylphosphine reduction cyclization obtain chloro- 7H- benzo [c] carbazole of 11-.
3. the synthetic method of chloro- 7H- benzo [c] carbazole of 11- according to claim 2, which is characterized in that closed in step 1
At 1- (the chloro- 6- nitrobenzophenone of 2-), specific step is as follows for-naphthalene:
Under agitation, 2,3- dichloronitrobenzene, 1- naphthalene boronic acids, basic salt, zeroth order palladium are added in the first organic solvent,
6-15h is reacted at 60-78 DEG C after mixing evenly, is cooled to room temperature after completion of the reaction, then reaction solution is extracted, is concentrated, again
Crystallization is to get 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene；
Wherein, 2,3- dichloronitrobenzene, 1- naphthalene boronic acids, basic salt, zeroth order palladium molar ratio be 1:1:1-4:0.005-0.02；2,
The amount ratio of 3- dichloronitrobenzene and the first organic solvent is 1g:5-20mL.
4. the synthetic method of chloro- 7H- benzo [c] carbazole of 11- according to claim 2, which is characterized in that closed in step 2
At chloro- 7H- benzo [c] carbazole of 11-, specific step is as follows:
Under agitation, that (the chloro- 6- nitrobenzophenone of the 2-)-naphthalene of 1- made from step 1 and triphenylphosphine are added to second is organic
In solvent, 0.5-2h is reacted at 150-240 DEG C, steams the second organic solvent after completion of the reaction, is then recrystallized to get 11-
Chloro- 7H- benzo [c] carbazole；
Wherein, 1- (the chloro- 6- nitrobenzophenone of 2-)-naphthalene, triphenylphosphine molar ratio be 1:2-3；1- (the chloro- 6- nitrobenzophenone of 2-)-
The amount ratio of naphthalene and the second organic solvent is 1g:5-10mL.
5. the synthetic method of chloro- 7H- benzo [c] carbazole of 11- according to claim 3, which is characterized in that the basic salt
For one of potassium phosphate, potassium carbonate, sodium carbonate, sodium bicarbonate.
6. the synthetic method of chloro- 7H- benzo [c] carbazole of 11- according to claim 5, which is characterized in that described first has
Solvent is one of toluene, dioxane, DMF, ethyl alcohol.
7. the synthetic method of chloro- 7H benzo-[c] carbazole of 11- according to claim 4, which is characterized in that the step 2
In, second organic solvent is 1,2- dichloro-benzenes or diphenyl ether.
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