CN103614134A - Organic electroluminescent material and preparation method thereof - Google Patents
Organic electroluminescent material and preparation method thereof Download PDFInfo
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Abstract
The invention relates to an organic electroluminescent material and a preparation method thereof, solving the technical problem that the luminescent efficiency of existing luminescent materials still can not meet the requirements of an OLED (organic light emitting diode). The novel organic electroluminescent material is synthesized by using 3-methyl-7H-benzacridine as a basis and introducing one of phenyl, p-methylphenyl and p-methoxyphenyl as well as a C10-C16 polycyclic aromatic hydrocarbon substituent group. Compared with 3-methyl-7H-benzacridine, the synthesized green organic electroluminescent material has a larger plane structure and conjugated system and can change the electron transition energy level, thus changing the luminescent spectrum, improving the luminescent efficiency and being capable of meeting the requirements of the OLED. The preparation method of the organic electroluminescent material, which is provided by the invention, is relatively simple in synthesis and purification, easy in purification of materials and low in cost, and can meet the requirements of industrialization development.
Description
Technical field
The present invention relates to organic photoelectrical material field, be specifically related to a kind of benzacridine olefines, electroluminescent organic material and preparation method thereof.
Background technology
Organic electroluminescent refers to that organic materials is under electric field action, is subject to electric current and exciting of electric field and luminous phenomenon.Organic electroluminescent LED (OLED) is to utilize this phenomenon to realize the technique of display of new generation showing.In the research of OLED, luminescent material selects to play conclusive effect.Lot of domestic and international research institution, enterprise are that the over-all properties that improves constantly luminescent material has been carried out a large amount of research work, have obtained abundant achievement in research.But the luminous efficiency of luminescent material still can not meet the requirement of OLED at present.
Acridine compound is to encircle greatly conjugated system, has rigid planar structure, is a kind of good fluorescent reagent.At present the research of acridine compound is mainly concentrated on, used as luminescence probe, for the application of Mian Yi ∕ DNA analysis, have very high luminous detection sensitivity.Acridine compound is also because having good insecticidal activity, antimalarial active, anti-tumor activity, and is widely used at aspects such as antibacterial, anti-inflammatory and antineoplastic agents.But the research that at present acridine compound is applied to organic electroluminescent field is less.
Summary of the invention
The present invention still can not meet the technical problem of the requirement of OLED for solving the luminous efficiency of existing luminescent material, and provide a kind of luminous efficiency higher, benzacridine olefines, electroluminescent organic material and preparation method thereof.
In order to solve the problems of the technologies described above, technical scheme of the present invention is specific as follows:
An electroluminescent organic material, the concrete structure general formula of this material as the formula (1):
In formula, R
1for phenyl, p-methylphenyl or p-methoxyphenyl; R
2for C
10-C
16fused ring aryl; Preferred R
2for 2-naphthyl or 2-pyrenyl.
Above-mentioned preferred electroluminescent organic material of the present invention, concrete structure is as shown in the chemical structural formula of 001-006:
Be exactly the concrete structure formation of this compound more above, but this series compound does not limit to and these listed chemical structures.Every take structural formula (1) as basis, R
1and R
2the arbitrary combination of the structure providing before group is respectively all should be included.
A preparation method for electroluminescent organic material, this preparation method's concrete steps and condition are as follows:
For 1:2.0～2.5, take 3-methyl-7H-benzacridine and R in molar ratio
2bromo-derivative, with toluene, dissolve; Add again potassium tert.-butoxide, acid chloride, tri-tert phosphorus; Under nitrogen protection condition, temperature of reaction is 80 ℃～90 ℃, reacts 10～15 hours; With the refining crude product obtaining of silica gel chromatography, obtain containing R
2substituent 3-methyl-7H-benzacridine; Wherein, the mol ratio of described potassium tert.-butoxide and 3-methyl-7H-benzacridine is 1.20～1.50:1, the mol ratio of described acid chloride and 3-methyl-7H-benzacridine is 0.013～0.017:1, and the mol ratio of described tri-tert phosphorus and 3-methyl-7H-benzacridine is 0.017～0.023:1;
In molar ratio for 1:1.2 takes containing R
2substituent 3-methyl-7H-benzacridine and MnO
2, drip 65% vitriol oil, by dissolution with solvents; React after 10～15 hours, through rotary evaporation, dry, obtain containing R
2substituent benzacridine aldehydes derivative;
Under nitrogen protection condition, add containing R
1substituent diethyl phosphoric acid and tetrahydrofuran (THF), be cooled to, after-65 ℃～-70 ℃, add potassium tert.-butoxide, reacts 2～2.5 hours; In reaction solution, drip containing R again
2substituent benzacridine aldehydes derivative, containing R
2substituent benzacridine aldehydes derivative and containing R
1the mol ratio of substituent diethyl phosphoric acid is 1:2.0～2.2; Continue reaction 2～2.5 hours, rise to room temperature, continue reaction after 2～2.5 hours, through separatory, extraction, dry, concentrated, recrystallization, obtain benzacridine alkenes compounds.
The invention has the beneficial effects as follows:
Electroluminescent organic material provided by the invention is to take 3-methyl-7H-benzacridine as basis, introduces a kind of in phenyl, p-methylphenyl and p-methoxyphenyl and a kind of C
10-C
16fused ring aryl, a synthetic class new Organic Electro Luminescent Materials.Compare with 3-methyl-7H-benzacridine, the synthetic electroluminescent organic material of the present invention has larger two dimensional structure and conjugated system, can, by regulating transition of electron to regulate luminous peak position, obtain required green electroluminescent organic material, and luminous efficiency obviously improve.
We are respectively by comparative sample 3-methyl-7H-benzacridine, compare with the luminous efficiency of the synthetic benzacridine alkenes compounds 001-006 of the embodiment of the present invention.Its result is: the luminous efficiency of 3-methyl-7H-benzacridine in dilute solution is 81%, and the luminous efficiency in film is 50%; And the luminous efficiency of the synthetic benzacridine alkenes compounds of the embodiment of the present invention in dilute solution is up to 96%, the luminous efficiency in film is up to 64%.By data comparison, we find that electroluminescent organic material provided by the invention is the higher material of a class luminous efficiency, can meet the requirement of OLED, have extraordinary application prospect.
The preparation method of electroluminescent organic material provided by the invention, the method synthetic and purify fairly simplely, material is easily purified, with low cost, can meet industrialization development requirement.
Embodiment
Electroluminescent organic material provided by the invention is with 3-methyl-7H-benzacridine and R
2bromo-derivative be raw material, reaction obtains containing R
2substituent 3-methyl-7H-benzacridine; In toluene solution, react with Manganse Dioxide again, generate containing R
2substituent benzacridine aldehyde compound, then with containing R
1substituent p diethylaminobenzoic acid ester cpds reaction, obtains benzacridine alkenes compounds, and its concrete synthetic route is as follows:
Wherein, the synthetic method of 3-methyl-7H-benzacridine is as follows:
Under nitrogen protection condition, will contain 1400g Na
2cO
3aqueous solution 6.5L, join the bromo-5-methylnaphthalene-1-of N-(8-yl) ethanamide 695g(2.50mol) in, 2-anisole ylboronic acid 380g(2.50mol) and 144g(Ph
3p)
4pd(125mmol, 5mol%) methyl ether 14ml.Mixture is refluxed 18 hours, then solvent is evaporated.In resistates, add 8L water, with methylene dichloride (2 * 5L) extracting twice, this extract Na
2sO
4be dried and evaporate.Column chromatography, with petrol ether/ethyl acetate mixture (1:1), re-crystallizing in ethyl acetate, obtains pure N-(8-(2-p-methoxy-phenyl)-5-methylnaphthalene-1-yl) ethanamide 450.42g, productive rate 59%, is clear crystal.
Under 0 ℃ of condition, by boron tribromide 1.5L(1M methylene dichloride, 1.50mol) be added drop-wise to N-(8-(2-p-methoxy-phenyl) naphthalene-1-yl) ethanamide 450.42g(1.47mol) in 4L dichloromethane solution, mixture is at room temperature stirred 18 hours, be then poured into water.Add saturated sodium bicarbonate, by ethyl acetate (2 * 3L) extracting twice.Merge organic extract liquid, use Na
2sO
4dry, and in underpressure distillation, column chromatography, as eluent, obtains white solid N-(8-(2-hydroxyphenyl)-5-methylnaphthalene-1-yl with ethyl acetate/dichloromethane mixture (1:1)) ethanamide 384.72g, productive rate 91%.
N-(8-(2-hydroxyphenyl)-5-methylnaphthalene-1-yl) solution ethanamide 384.72g(1.32mol) stirs 40 hours under the mixture of the hydrazine hydrate 4.0L of Pentyl alcohol 6.0L and 80% is refluxing, then the pressure of vapourisation under reduced pressure.Column chromatography, as eluent, obtains brown product 3-methyl-7H-benzacridine 178.09g, productive rate 77% by ethyl acetate/petroleum ether (1:1).
Embodiment 1: compound 001 synthetic
Concrete synthetic route is as follows:
Take 3-methyl-7H-benzacridine 69.38g, 2-bromonaphthalene 124.24g, potassium tert.-butoxide 40.38g, acid chloride (II) 1.23g, tri-tert phosphorus 1.35g, dissolves with 250ml toluene, under nitrogen protection, in 80 ℃ of reactions 10 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, then carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains 3-methyl-7-(2-naphthyl)-7H-benzacridine 91.14g, productive rate 85%.
To 3-methyl-7-(2-naphthyl) add 26.60g MnO in-7H-benzacridine 91.14g
2, 65% H
2sO
410ml, dissolves with 250ml toluene, reacts 12 hours, obtains 7-(2-naphthyl)-7H-benzacridine-3-formaldehyde 89.47g, productive rate 95%.
Under nitrogen protection condition; add benzyl diethyl phosphoric acid 38.06g and tetrahydrofuran (THF) 200ml; be cooled to after-65 ℃; add potassium tert.-butoxide 18.2g; react after 2 hours, in reaction solution, drip 360ml7-(2-naphthyl) tetrahydrofuran solution of-7H-benzacridine-3-formaldehyde (29.71g), continued reaction after 2 hours; warming while stirring, to room temperature, continues reaction 2 hours.In the reaction solution of gained, add separatory after distilled water, toluene, form water layer and organic layer.With toluene, extract after this water layer, this toluene and organic layer are merged, with saturated aqueous common salt, clean, with anhydrous sodium sulfate drying, concentrated, use toluene recrystallization, the solid of gained is carried out to drying under reduced pressure, result obtains the white-yellowish solid 7-(2-naphthyl of 25.66g)-3-styryl-7H-benzacridine, productive rate 72%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 445.55; Test value is 445.57.Ultimate analysis: calculated value is C:91.65%; H:5.20%; N:3.14%; Test value is C:91.63%; H:5.03%; N:3.15%.
Embodiment 2: compound 002 synthetic
Concrete synthetic route is as follows:
Take 3-methyl-7H-benzacridine 69.38g, 2-bromonaphthalene 124.24g, potassium tert.-butoxide 40.38g, acid chloride (II) 1.23g, tri-tert phosphorus 1.35g, dissolves with 250ml toluene, under nitrogen protection, in 80 ℃ of reactions 10 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, then carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains 3-methyl-7-(2-naphthyl)-7H-benzacridine 91.14g, productive rate 85%.
To 3-methyl-7-(2-naphthyl) add 26.60g MnO in-7H-benzacridine 91.14g
2, 65% H
2sO
410ml, dissolves with 250ml toluene, reacts 12 hours, obtains 7-(2-naphthyl)-7H-benzacridine-3-formaldehyde 89.47g, productive rate 95%.
Under nitrogen protection condition; add 4-aminomethyl phenyl diethyl phosphoric acid 40.39g and tetrahydrofuran (THF) 200ml; be cooled to after-70 ℃; add potassium tert.-butoxide 18.2g; react after 2.5 hours, in reaction solution, drip 360ml7-(2-naphthyl) tetrahydrofuran solution of-7H-benzacridine-3-formaldehyde (29.71g), continued reaction after 2.5 hours; warming while stirring, to room temperature, continues reaction 2.5 hours.In the reaction solution of gained, add separatory after distilled water, toluene, form water layer and organic layer.With toluene, extract after this water layer, this toluene and organic layer are merged, with saturated aqueous common salt, clean, with anhydrous sodium sulfate drying, concentrated, use toluene recrystallization, the solid of gained is carried out to drying under reduced pressure, result obtains the white-yellowish solid 3-(4-vinyl toluene base of 26.81g)-7-(2-naphthyl)-7H-benzacridine, productive rate 73%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 459.58; Test value is 459.56.Ultimate analysis: calculated value is C:91.47%; H:5.48%; N:3.05%; Test value is C:91.49%; H:5.50%; N:3.01%.
Embodiment 3: compound 003 synthetic
Concrete synthetic route is as follows:
Take 3-methyl-7H-benzacridine 69.38g, 2-bromonaphthalene 124.24g, potassium tert.-butoxide 40.38g, acid chloride (II) 1.23g, tri-tert phosphorus 1.35g, dissolves with 250ml toluene, under nitrogen protection, in 80 ℃ of reactions 10 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, then carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains 3-methyl-7-(2-naphthyl)-7H-benzacridine 91.14g, productive rate 85%.
To 3-methyl-7-(2-naphthyl) add 26.60g MnO in-7H-benzacridine 91.14g
2, 65% H
2sO
410ml, dissolves with 250ml toluene, reacts 12 hours, obtains 7-(2-naphthyl)-7H-benzacridine-3-formaldehyde 89.47g, productive rate 95%.
Under nitrogen protection condition; add 4-p-methoxy-phenyl diethyl phosphoric acid 43.06g and tetrahydrofuran (THF) 200ml; be cooled to after-65 ℃; add potassium tert.-butoxide 18.2g; react after 2 hours, in reaction solution, drip 360ml7-(2-naphthyl) tetrahydrofuran solution of-7H-benzacridine-3-formaldehyde (29.71g), continued reaction after 2 hours; warming while stirring, to room temperature, continues reaction 2 hours.In the reaction solution of gained, add separatory after distilled water, toluene, form water layer and organic layer.With toluene, extract after this water layer, this toluene and organic layer are merged, with saturated aqueous common salt, clean, with anhydrous sodium sulfate drying, concentrated, use toluene recrystallization, the solid of gained is carried out to drying under reduced pressure, result obtains the white-yellowish solid 3-(4-methoxyl-styrene of 27.01g)-7-(2-naphthyl)-7H-benzacridine, productive rate 71%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 475.58; Test value is 475.56.Ultimate analysis: calculated value is C:88.39%; H:5.30%; N:2.95%; O:3.36%; Test value is C:88.37%; H:5.32%; N:2.93%; O:3.38%.
Embodiment 4: compound 004 synthetic
Concrete synthetic route is as follows:
Take 3-methyl-7H-benzacridine 69.38g, 2-bromine pyrene 168.69g, potassium tert.-butoxide 40.38g, acid chloride (II) 1.23g, tri-tert phosphorus 1.35g, dissolves with 250ml toluene, under nitrogen protection, in 80 ℃ of reactions 10 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, then carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains 100.97g yellow-white 3-methyl-7-(2-pyrenyl)-7H-benzacridine, productive rate 78%.
To 3-methyl-7-(2-naphthyl) add 24.41g MnO in-7H-benzacridine 100.97g
2, 65% H
2sO
410ml, dissolves with 250ml toluene, reacts 14 hours, obtains 7-(2-naphthyl)-7H-benzacridine-3-formaldehyde 97.99g, productive rate 94%.
Under nitrogen protection condition; add benzyl diethyl phosphoric acid 38.06g and tetrahydrofuran (THF) 200ml; be cooled to after-65 ℃; add potassium tert.-butoxide 18.2g; react after 2 hours, in reaction solution, drip 360ml7-(2-pyrenyl) tetrahydrofuran solution of-7H-benzacridine-3-formaldehyde (31.18g), continued reaction after 2 hours; warming while stirring, to room temperature, continues reaction 2 hours.In the reaction solution of gained, add separatory after distilled water, toluene, form water layer and organic layer.With toluene, extract after this water layer, this toluene and organic layer are merged, with saturated aqueous common salt, clean, with anhydrous sodium sulfate drying, concentrated, use toluene recrystallization, the solid of gained is carried out to drying under reduced pressure, result obtains the white-yellowish solid 7-(2-pyrenyl of 25.51g)-3-styryl-7H-benzacridine, productive rate 72%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 519.63; Test value is 519.62.Ultimate analysis: calculated value is C:92.46%; H:4.85%; N:2.70%; Test value is C:92.45%; H:4.84%; N:2.71%.
Embodiment 5: compound 005 synthetic
Concrete synthetic route is as follows:
Take 3-methyl-7H-benzacridine 69.38g, 2-bromine pyrene 168.69g, potassium tert.-butoxide 40.38g, acid chloride (II) 1.23g, tri-tert phosphorus 1.35g, dissolves with 250ml toluene, under nitrogen protection, in 80 ℃ of reactions 10 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, then carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains 100.97g yellow-white 3-methyl-7-(2-pyrenyl)-7H-benzacridine, productive rate 78%.
To 3-methyl-7-(2-naphthyl) add 24.41g MnO in-7H-benzacridine 100.97g
2, 65% H
2sO
410ml, dissolves with 250ml toluene, reacts 14 hours, obtains 7-(2-naphthyl)-7H-benzacridine-3-formaldehyde 97.99g, productive rate 94%.
Under nitrogen protection condition; add 4-aminomethyl phenyl diethyl phosphoric acid 40.39g and tetrahydrofuran (THF) 200ml; be cooled to after-70 ℃; add potassium tert.-butoxide 18.2g; react after 2.5 hours, in reaction solution, drip 360ml7-(2-pyrenyl) tetrahydrofuran solution of-7H-benzacridine-3-formaldehyde (31.18g), continued reaction after 2.5 hours; warming while stirring, to room temperature, continues reaction 2.5 hours.In the reaction solution of gained, add separatory after distilled water, toluene, form water layer and organic layer.With toluene, extract after this water layer, this toluene and organic layer are merged, with saturated aqueous common salt, clean, with anhydrous sodium sulfate drying, concentrated, use toluene recrystallization, the solid of gained is carried out to drying under reduced pressure, result obtains the white-yellowish solid 3-(4-vinyl toluene base of 27.64g)-7-(2-pyrenyl)-7H-benzacridine, productive rate 74%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 533.66; Test value is 533.67.Ultimate analysis: calculated value is C:92.28%; H:5.10%; N:2.62%; Test value is C:92.26%; H:5.11%; N:2.63%.
Embodiment 6: compound 006 synthetic
Concrete synthetic route is as follows:
Take 3-methyl-7H-benzacridine 69.38g, 2-bromine pyrene 168.69g, potassium tert.-butoxide 40.38g, acid chloride (II) 1.23g, tri-tert phosphorus 1.35g, dissolves with 250ml toluene, under nitrogen protection, in 80 ℃ of reactions 10 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, then carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains 100.97g yellow-white 3-methyl-7-(2 – pyrenyl)-7H-benzacridine, productive rate 78%.
To 3-methyl-7-(2-naphthyl) add 24.41g MnO in-7H-benzacridine 100.97g
2, 65% H
2sO
410ml, dissolves with 250ml toluene, reacts 14 hours, obtains 7-(2-naphthyl)-7H-benzacridine-3-formaldehyde 97.99g, productive rate 94%.
Under nitrogen protection condition; add 4-p-methoxy-phenyl diethyl phosphoric acid 43.06g and tetrahydrofuran (THF) 200ml; be cooled to after-65 ℃; add potassium tert.-butoxide 18.2g; react after 2 hours, in reaction solution, drip 360ml7-(2-pyrenyl) tetrahydrofuran solution of-7H-benzacridine-3-formaldehyde (31.18g), continued reaction after 2 hours; warming while stirring, to room temperature, continues reaction 2 hours.In the reaction solution of gained, add separatory after distilled water, toluene, form water layer and organic layer.With toluene, extract after this water layer, this toluene and organic layer are merged, with saturated aqueous common salt, clean, with anhydrous sodium sulfate drying, concentrated, use toluene recrystallization, the solid of gained is carried out to drying under reduced pressure, result obtains the white-yellowish solid 3-(4-methoxyl-styrene of 27.31g)-7-(2-pyrenyl)-7H-benzacridine, productive rate 71%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 549.66; Test value is 549.67.Ultimate analysis: calculated value is C:89.59%; H:4.95%; N:2.55%; O:2.91%; Test value is C:89.57%; H:4.96%; N:2.54%; O:2.90%.
Simultaneous test
We respectively by comparative sample 3-methyl-7H-benzacridine, to be mixed with respectively concentration with the synthetic benzacridine alkenes compounds 001-006 of embodiment of the present invention 1-6 be 1 * 10
-6the solution of mol/L, is used Edinburdh-FL S920 equipment, and spin-coating method is made into film, has tested respectively their luminous efficiencies in dilute solution neutralized film, and concrete data are as table 1.
The luminous efficiency of table 1 benzacridine alkenes compounds 001-006 and comparative sample
| Compound | Luminous efficiency in dilute solution | Luminous efficiency in film |
| Comparative sample | 81% | 50% |
| 001 | 91% | 59% |
| 002 | 92% | 62% |
| 003 | 92% | 61% |
| 004 | 90% | 60% |
| 005 | 93% | 59% |
| 006 | 96% | 64% |
From the data of table 1, can find out, the luminous efficiency of comparative sample 3-methyl-7H-benzacridine in dilute solution is 81%, and the luminous efficiency in film is 50%; And the luminous efficiency of the synthetic benzacridine alkenes compounds of the embodiment of the present invention in dilute solution is up to 96%, the luminous efficiency in film is up to 64%.Be that the luminous efficiency of benzacridine alkenes compounds provided by the invention in dilute solution, the luminous efficiency in film are all significantly improved.By data comparison, we find that electroluminescent organic material provided by the invention is the higher material of a class luminous efficiency, can meet the requirement of OLED, have extraordinary application prospect.
Should be understood that, application of the present invention is not limited to above-mentioned giving an example, and for those of ordinary skills, can be improved according to the above description or convert, and all these improvement and conversion all should belong to the protection domain of claims of the present invention.
Claims (3)
1. an electroluminescent organic material, is characterized in that, the concrete structure general formula of this material as the formula (1):
In formula, R
1for phenyl, p-methylphenyl or p-methoxyphenyl; R
2for C
10-C
16condensed-nuclei aromatics.
2. electroluminescent organic material according to claim 1, is characterized in that, R
2for 2-naphthyl or 2-pyrenyl.
3. the preparation method of electroluminescent organic material according to claim 1 and 2, is characterized in that, this preparation method's concrete steps and condition are as follows:
For 1:2.0～2.5, take 3-methyl-7H-benzacridine and R in molar ratio
2bromo-derivative, with toluene, dissolve; Add again potassium tert.-butoxide, acid chloride, tri-tert phosphorus; Under nitrogen protection condition, temperature of reaction is 80 ℃～90 ℃, reacts 10～15 hours; With the refining crude product obtaining of silica gel chromatography, obtain containing R
2substituent 3-methyl-7H-benzacridine; Wherein, the mol ratio of described potassium tert.-butoxide and 3-methyl-7H-benzacridine is 1.20～1.50:1, the mol ratio of described acid chloride and 3-methyl-7H-benzacridine is 0.013～0.017:1, and the mol ratio of described tri-tert phosphorus and 3-methyl-7H-benzacridine is 0.017～0.023:1;
In molar ratio for 1:1.2 takes containing R
2substituent 3-methyl-7H-benzacridine and MnO
2, drip 65% vitriol oil, by dissolution with solvents; React after 10～15 hours, through rotary evaporation, dry, obtain containing R
2substituent benzacridine aldehydes derivative;
Under nitrogen protection condition, add containing R
1substituent diethyl phosphoric acid and tetrahydrofuran (THF), be cooled to, after-65 ℃～-70 ℃, add potassium tert.-butoxide, reacts 2～2.5 hours; In reaction solution, drip containing R again
2substituent benzacridine aldehydes derivative, containing R
2substituent benzacridine aldehydes derivative and containing R
1the mol ratio of substituent diethyl phosphoric acid is 1:2.0～2.2; Continue reaction 2～2.5 hours, rise to room temperature, continue reaction after 2～2.5 hours, through separatory, extraction, dry, concentrated, recrystallization, obtain benzacridine alkenes compounds.
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| US20150048323A1 (en) * | 2013-08-13 | 2015-02-19 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light-emitting device including the same |
| WO2018138306A1 (en) * | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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| CN102229565A (en) * | 2011-05-10 | 2011-11-02 | 南京邮电大学 | Spirofluorene bisbenzoacridine organic semiconductor material, preparation method and use method thereof |
| CN102702072A (en) * | 2012-06-26 | 2012-10-03 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent material of large-pi conjugated system and preparation method and application thereof |
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| US20150048323A1 (en) * | 2013-08-13 | 2015-02-19 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light-emitting device including the same |
| US9564601B2 (en) * | 2013-08-13 | 2017-02-07 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light-emitting device including the same |
| WO2018138306A1 (en) * | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| CN110167940A (en) * | 2017-01-30 | 2019-08-23 | 默克专利有限公司 | Material for organic electroluminescence device |
| US11407766B2 (en) | 2017-01-30 | 2022-08-09 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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