CN102627570B - Synthetic method of 1,4-bis[4-(di-m-methylphenylamino)styryl]benzene - Google Patents
Synthetic method of 1,4-bis[4-(di-m-methylphenylamino)styryl]benzene Download PDFInfo
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- CN102627570B CN102627570B CN201210073634.0A CN201210073634A CN102627570B CN 102627570 B CN102627570 B CN 102627570B CN 201210073634 A CN201210073634 A CN 201210073634A CN 102627570 B CN102627570 B CN 102627570B
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Abstract
The invention discloses a synthetic method of 1,4-bis[4-(di-m-methylphenylamino)styryl]benzene. The synthetic method comprises the following steps: adding N,N-di(3-methylphenyl)-4-aminobenzaldehyde, p-dibenzyl diethyl phosphate benzene, sodium tert-butoxide and N,N-dimethyl acetamide to a reaction bottle at normal temperature, stirring to dissolve them, reacting by putting the reaction bottle into a microwave chemical reactor for 3-10min under conditions that the microwave radiation power is 800W, pouring the resulting reaction solution to 100ml of methanol, filtering, and recrystallizing with toluene to obtain 1,4-bis[4-(di-m-methylphenylamino)styryl]benzene. The synthetic method is mainly used to prepare 1,4-bis[4-(di-m-methylphenylamino)styryl]benzene.
Description
Technical field
The present invention relates to a kind of synthetic method of styryl triarylamine derivative, specifically relate to the synthetic method of Isosorbide-5-Nitrae-bis-[4-(two tolyl amino) styryl] benzene.
Background technology
Since ORGANIC ELECTROLUMINESCENCE DISPLAYS technology is invented, because its low-voltage driving, active illuminating characteristic and potential low cost have received people's very big concern, started to step into the industrialization stage simultaneously.Organic electroluminescent reality technology, with its remarkable technical feature, threatens and challenge various demonstration product slate, and it is the optimal technique of display of future generation most with development prospect that shown industrial community is known as.
Blue organic electroluminescent display device, applies quite extensively, and except can be used as common information display part, simultaneously according to the principle of three primary colours, blue-light-emitting is display white and the colored basis showing.The luminescent layer of blue organic electroluminescent device generally contains Blue-light emitting host material and blue light dopant material.
In order to improve purity of color and the luminous efficiency of luminescent device, conventionally in main body luminescent material, add a small amount of dopant material, the wavelength of main body changes according to the wavelength of dopant material, therefore according to the kind of dopant material, can obtain the light with required wavelength.
US Patent No. 20080001123 discloses a series of styrenic derivatives that can be used as blue light dopant material, comprising two [4-(two the tolyl amino) styryl] benzene of Isosorbide-5-Nitrae.Its structural formula is as follows:
But this patent is not reported the synthetic method of this compound.
Summary of the invention
The main technical solution problem of the present invention is to overcome shortcomings and deficiencies of the prior art, and the synthetic method of a kind of Isosorbide-5-Nitrae-bis-[4-(two tolyl amino) styryl] benzene is provided.
Synthetic route of the present invention is as follows:
The synthetic method of Isosorbide-5-Nitrae of the present invention-bis-[4-(two tolyl amino) styryl] benzene, its structural formula is as follows:
Comprise the following steps: at normal temperatures by N, N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde, to dibenzyl diethyl phosphoric acid benzene, sodium tert-butoxide and N, N-N,N-DIMETHYLACETAMIDE adds in reaction flask, after stirring and dissolving, reaction flask is put into microwave chemical reactor, at microwave irradiation power, be 800W reaction 3～10min, be cooled to after room temperature, reaction solution is poured in 100mL methyl alcohol, filter, resulting filter cake is with obtaining 1 after toluene recrystallization, two [4-(two the tolyl amino) styryl] benzene of 4-, wherein to dibenzyl diethyl phosphoric acid benzene, N, the mol ratio of N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde and sodium tert-butoxide is 1: 2～3: 2～3.
The synthetic method of the preferred Isosorbide-5-Nitrae of the present invention-bis-[4-(two tolyl amino) styryl] benzene, comprises the following steps:
At normal temperatures by 3.78g (10mmol) to dibenzyl diethyl phosphoric acid benzene, 7.53g (25mmol) N, N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde, 2.4g (25mmol) sodium tert-butoxide and 50mL N, N-N,N-DIMETHYLACETAMIDE, join in 250mL reaction flask, after stirring and dissolving, reaction flask is put into microwave chemical reactor, setting microwave power is 800W, reaction times is 5min, be cooled to after room temperature, reaction product is poured in 100mL methyl alcohol and stirred, the standing yellow solid of separating out, filter, the filter cake obtaining is with obtaining glassy yellow pressed powder after toluene recrystallization, after dry, obtain 1, two [4-(two tolyl amino) styryl] the benzene 6.11g of 4-, yield is 91%, purity is 99.5%.
Beneficial effect of the present invention:
The synthetic method reaction times of the present invention is shorter, be only 3min, synthetic method reaction yield of the present invention is higher, its reaction yield can reach 91%, synthetic method of the present invention obtains Isosorbide-5-Nitrae-bis-[4-(two tolyl amino) styryl] benzene can obtain high-purity product through recrystallization, and its product purity can reach 99.5%, and the synthetic method of Isosorbide-5-Nitrae-bis-[4-(two tolyl amino) styryl] benzene is not reported in documents.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail.
Microwave chemical reactor is that magnificent WBFY-201 type is given in Gongyi.
Embodiment 1
At normal temperatures by 3.78g (10mmol) to dibenzyl diethyl phosphoric acid benzene, 6.02g (20mmol) N, N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde, 1.92g (20mmol) sodium tert-butoxide and 50mL N, N-N,N-DIMETHYLACETAMIDE, join in 250mL reaction flask, after stirring and dissolving, reaction flask is put into microwave chemical reactor, setting microwave power is 800W, reaction times is 3min, after reaction finishes, reaction solution is cooled to room temperature, reaction product is poured in 100mL methyl alcohol and stirred, the standing yellow solid of separating out, filter, the filter cake obtaining is with obtaining glassy yellow pressed powder after toluene recrystallization, after dry, obtain 1, two [4-(two tolyl amino) styryl] the benzene 5.98g of 4-, yield is 89%, purity is 99.0%.
Structural Identification
1HNMR(CDCl
3，500MHz)：δ7.46(s，4H)，δ7.36～7.38(d，4H)，δ7.13～7.16(t，4H)，δ6.97～7.08(m，8H)，δ6.93(s，4H)，δ6.89～6.91(d，4H)，δ6.84～6.86(d，4H)，δ2.27(s，12H)。
Ultimate analysis:
Theoretical value: C, 89.25; H, 6.59; N, 4.16;
Measured value: C, 89.22; H, 6.60; N, 4.18.
Above-mentioned appraising datum confirms that the material of gained is Isosorbide-5-Nitrae-bis-[4-(two tolyl amino) styryl] benzene really.
Embodiment 2
At normal temperatures by 3.78g (10mmol) to dibenzyl diethyl phosphoric acid benzene, 7.53g (25mmol) N, N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde, 2.4g (25mmol) sodium tert-butoxide and 50mL N, N-N,N-DIMETHYLACETAMIDE, join in 250mL reaction flask, after stirring and dissolving, reaction flask is put into microwave chemical reactor, setting microwave power is 800W, reaction times is 3min, after reaction finishes, reaction solution is cooled to room temperature, reaction product is poured in 100mL methyl alcohol and stirred, the standing yellow solid of separating out, filter, the filter cake obtaining is with obtaining glassy yellow pressed powder after toluene recrystallization, after dry, obtain 1, two [4-(two tolyl amino) styryl] the benzene 6.05g of 4-, yield is 90%, purity is 99.2%.
Embodiment 3
At normal temperatures by 3.78g (10mmol) to dibenzyl diethyl phosphoric acid benzene, 7.53g (25mmol) N, N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde, 2.4g (25mmol) sodium tert-butoxide and 50mL N, N-N,N-DIMETHYLACETAMIDE, join in 250mL reaction flask, after stirring and dissolving, reaction flask is put into microwave chemical reactor, setting microwave power is 800W, reaction times is 5min, after reaction finishes, reaction solution is cooled to room temperature, reaction product is poured in 100mL methyl alcohol and stirred, the standing yellow solid of separating out, filter, the filter cake obtaining is with obtaining glassy yellow pressed powder after toluene recrystallization, after dry, obtain 1, two [4-(two tolyl amino) styryl] the benzene 6.11g of 4-, yield is 91%, purity is 99.5%.
Embodiment 4
At normal temperatures by 3.78g (10mmol) to dibenzyl diethyl phosphoric acid benzene, 7.53g (25mmol) N, N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde, 2.4g (25mmol) sodium tert-butoxide and 50mL N, N-N,N-DIMETHYLACETAMIDE, join in 250mL reaction flask, after stirring and dissolving, reaction flask is put into microwave chemical reactor, setting microwave power is 800W, reaction times is 10min, after reaction finishes, reaction solution is cooled to room temperature, reaction product is poured in 100mL methyl alcohol and stirred, the standing yellow solid of separating out, filter, the filter cake obtaining is with obtaining glassy yellow pressed powder after toluene recrystallization, after dry, obtain 1, two [4-(two tolyl amino) styryl] the benzene 5.84g of 4-, yield is 87%, purity is 99.0%.
Embodiment 5
At normal temperatures by 3.78g (10mmol) to dibenzyl diethyl phosphoric acid benzene, 9.03g (30mmol) N, N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde, 2.88g (30mmol) sodium tert-butoxide and 50mL N, N-N,N-DIMETHYLACETAMIDE, join in 250mL reaction flask, after stirring and dissolving, reaction flask is put into microwave chemical reactor, setting microwave power is 800W, reaction times is 10min, after reaction finishes, reaction solution is cooled to room temperature, reaction product is poured in 100mL methyl alcohol and stirred, the standing yellow solid of separating out, filter, the filter cake obtaining is with obtaining glassy yellow pressed powder after toluene recrystallization, after dry, obtain 1, two [4-(two tolyl amino) styryl] the benzene 5.91g of 4-, yield is 88%, purity is 99.0%.
Claims (2)
1. the synthetic method of two [4-(two the tolyl amino) styryl] benzene of 4-, its structural formula is as follows:
Comprise the following steps: normal temperature is by N, N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde, terephthaldehyde's base ethyl diphosphonic acid, sodium tert-butoxide and N, N-N,N-DIMETHYLACETAMIDE adds in reaction flask, after stirring and dissolving, reaction flask is put into microwave chemical reactor, at microwave irradiation power, be 800W reaction 3～10min, be cooled to after room temperature, reaction solution is poured in 100mL methyl alcohol, filter, after resulting filter cake toluene recrystallization, obtain 1, two [4-(two the tolyl amino) styryl] benzene of 4-, terephthaldehyde's base ethyl diphosphonic acid wherein, N, the mol ratio of N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde and sodium tert-butoxide is 1:2～3:2～3.
2. according to claim 11, the synthetic method of two [4-(two the tolyl amino) styryl] benzene of 4-, comprise the following steps: normal temperature is by 10mmol terephthaldehyde base ethyl diphosphonic acid 3.78g, 25mmol N, N-bis-(3-aminomethyl phenyl)-4-aminobenzaldehyde 7.53g, 25mmol sodium tert-butoxide 2.4g and 50mLN, N-N,N-DIMETHYLACETAMIDE, join in 250mL reaction flask, after stirring and dissolving, reaction flask is put into microwave chemical reactor, setting microwave power is 800W, reaction times is 5min, be cooled to after room temperature, reaction product is poured in 100mL methyl alcohol and stirred, the standing yellow solid of separating out, filter, the filter cake obtaining is with obtaining glassy yellow pressed powder after toluene recrystallization, after dry, obtain 1, two [4-(two tolyl amino) styryl] the benzene 6.11g of 4-, yield is 91%, purity is 99.5%.
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