CN103614133A - Organic electroluminescent material and preparation method thereof - Google Patents
Organic electroluminescent material and preparation method thereof Download PDFInfo
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- CN103614133A CN103614133A CN201310551975.9A CN201310551975A CN103614133A CN 103614133 A CN103614133 A CN 103614133A CN 201310551975 A CN201310551975 A CN 201310551975A CN 103614133 A CN103614133 A CN 103614133A
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- benzacridine
- organic electroluminescent
- electroluminescent material
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- TWGGCWKXYVWYLO-UHFFFAOYSA-N CC(CC=C1)C2=C1N(C(CC1)c3ccc(cc4)c5c3C1(C)C=Cc5c4N(c1c-3cccc1)c1cccc4c1c-3ccc4)c1c3c2cccc3ccc1 Chemical compound CC(CC=C1)C2=C1N(C(CC1)c3ccc(cc4)c5c3C1(C)C=Cc5c4N(c1c-3cccc1)c1cccc4c1c-3ccc4)c1c3c2cccc3ccc1 TWGGCWKXYVWYLO-UHFFFAOYSA-N 0.000 description 1
- IQVYSFXSBYGSSY-UHFFFAOYSA-N CC1(C)C(C=[I]C=C2)=C2c2c1cccc2 Chemical compound CC1(C)C(C=[I]C=C2)=C2c2c1cccc2 IQVYSFXSBYGSSY-UHFFFAOYSA-N 0.000 description 1
- MCXFBJRDLNFXHM-UHFFFAOYSA-N c(cc1-2)ccc1Nc1cccc3c1c-2ccc3 Chemical compound c(cc1-2)ccc1Nc1cccc3c1c-2ccc3 MCXFBJRDLNFXHM-UHFFFAOYSA-N 0.000 description 1
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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 7H-benzacridine as a basis and introducing a polycyclic aromatic group on the basis. Compared with 7H-benzacridine, the organic electroluminescent material provided by the invention has a better plane structure and conjugated system and can adjust the luminescent peak by adjusting electron transition to obtain the needed green organic electroluminescent material. The luminescent efficiency of the organic electroluminescent material is obviously improved. The preparation method of the organic electroluminescent material, which is provided by the invention, is relatively simple in synthesis and purification 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 electroluminescent organic material of a kind of pair of benzacridine class and preparation method thereof.
Background technology
Organic electroluminescent (OEL) 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, the selection of organic materials plays conclusive effect.The organic materials of using in OLED mainly contains hole-injecting material, hole mobile material, luminescent material, electron transport material and electron injection material etc., and luminescent material is main raw wherein.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 is high, two benzacridine classes, 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, the concrete structure formula of A is as follows, the site that wherein * representative is connected with the nitrogen-atoms of benzacridine;
The concrete structure formula of the electroluminescent organic material that the concrete structure formula of above-mentioned A is corresponding corresponds to respectively the chemical structural formula of following 001-006:
The preparation method of electroluminescent organic material, this preparation method's concrete steps and condition are as follows:
For 1:3.0～3.5, take in molar ratio two bromo-derivatives and the 7H-benzacridine of A, with toluene, dissolve; Add again potassium tert.-butoxide, acid chloride, tri-tert phosphorus; Wherein the mol ratio of potassium tert.-butoxide and 7H-benzacridine is 0.40～0.45:1, and the mol ratio of acid chloride and 7H-benzacridine is 0.006～0.010:1, and the mol ratio of tri-tert phosphorus and 7H-benzacridine is 0.004～0.010:1;
Under nitrogen protection condition, by the mixing solutions of above-mentioned reactant, in temperature of reaction, be 80 ℃～90 ℃, react 10～15 hours; Cooling, filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, then carry out recrystallization, obtain two benzacridine compounds after dry the crude product obtaining with toluene.
The invention has the beneficial effects as follows:
Electroluminescent organic material provided by the invention is to take 7H-benzacridine as basis, introduces on this basis the synthetic class new Organic Electro Luminescent Materials of condensed ring aromatic group.Compare with 7H-benzacridine, electroluminescent organic material provided by the invention has better 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 7H-benzacridine, compare with the luminous efficiency of the synthetic two benzacridine compounds 001-006 of the embodiment of the present invention.Its result is: the luminous efficiency of 7H-benzacridine in dilute solution is 80%, and the luminous efficiency in film is 49%; And the luminous efficiency of two benzacridine compounds that the embodiment of the present invention is synthesized 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, it is synthetic and purify fairly simplely, with low cost, can meet industrialization development demand.The productive rate of product increases substantially, and purity is high, and HPLC purity is greater than 98%.
Embodiment
Electroluminescent organic material provided by the invention, is that to take two bromo-derivatives of 7H-benzacridine and A be raw material, and reaction obtains containing substituent pair of benzacridine compounds of A, and its concrete synthetic route is as follows:
The synthetic route of 7H-benzacridine is as follows:
Under nitrogen protection condition, will contain Na
2cO
3(1400g) water 6.5L, joins N-(8-bromonaphthalene-1-yl) ethanamide 660g(2.50mol) in solution, (6-methoxy basic ring six-1,5-diene-1-yl) boric acid 505g(2.50mol), and 144g(Ph
3p)
4pd(125mmol, 5mol%) methyl ether 14ml.Mixture is refluxed 18 hours, then solvent is evaporated.To 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) naphthalene-1-yl) ethanamide 308.82g, productive rate 55%, 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 308.82g(1.06mol) 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.The organic extract liquid merging, uses Na
2sO
4dry, and in underpressure distillation, column chromatography, as eluent, obtains white solid N-(8-(2-hydroxy phenyl) naphthalene-1-yl with ethyl acetate/dichloromethane mixture (1:1)) ethanamide 271.77g, productive rate 92%.
N-(8-(2-hydroxy phenyl) naphthalene-1-yl) solution ethanamide 271.77g(0.98mol) 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 7H-benzacridine 173.82g, productive rate 79% by ethyl acetate/petroleum ether (1:1).
Embodiment 1: compound 001 synthetic
Concrete synthetic route is as follows:
Take 1,6-dibromo pyrene 35.79g, 7H-benzacridine 64.18g, potassium tert.-butoxide 13.46g, acid chloride (II) 0.41g, tri-tert phosphorus 0.45g, 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 the two benzacridine compounds 001 of 53.78g white-yellowish solid, and productive rate is more than 85%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 632.75; Test value is 632.73.Ultimate analysis: calculated value is C:91.11%; H:4.46%; N:4.43%; Test value is C:91.13%; H:4.47%; N:4.40%.
Embodiment 2: compound 002 synthetic
Concrete synthetic route is as follows:
Take 2,7-bis-bromo-9,9-dimethyl fluorene 35.20g, 7H-benzacridine 67.35g, potassium tert.-butoxide 14.36g, acid chloride (II) 0.48g, tri-tert phosphorus 0.54g, dissolved with 250ml toluene, in 82 ℃ of reactions 11 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains the two benzacridine compounds 002 of 51.85g white-yellowish solid, and productive rate is more than 83%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 624.77; Test value is 624.75.Ultimate analysis: calculated value is C:90.35%; H:5.16%; N:4.48%; Test value is C:90.34%; H:5.18%; N:4.47%.
Embodiment 3: compound 003 synthetic
Concrete synthetic route is as follows:
Take 9,10-dibromoanthracene 33.60g, 7H-benzacridine 69.52g, potassium tert.-butoxide 15.26g, acid chloride (II) 0.56g, tri-tert phosphorus 0.63g, dissolved with 250ml toluene, in 84 ℃ of reactions 12 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains the two benzacridine compounds 003 of 52.35g white-yellowish solid, and productive rate is more than 86%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 608.73; Test value is 608.71.Ultimate analysis: calculated value is C:90.76%; H:4.64%; N:4.60%; Test value is C:90.77%; H:4.63%; N:4.59%.
Embodiment 4: compound 004 synthetic
Concrete synthetic route is as follows:
Take the luxuriant and rich with fragrance 33.60g of 2,7-dibromo, 7H-benzacridine 71.69g, potassium tert.-butoxide 16.16g, acid chloride (II) 0.64g, tri-tert phosphorus 0.72g, dissolved with 250ml toluene, in 86 ℃ of reactions 13 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains the two benzacridine compounds 004 of 51.13g white-yellowish solid, and productive rate is more than 84%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 608.73; Test value is 608.71.Ultimate analysis: calculated value is C:90.76%; H:4.64%; N:4.60%; Test value is C:90.75%; H:4.65%; N:4.58%.
Embodiment 5: compound 005 synthetic
Concrete synthetic route is as follows:
Take 3,9-bis-Xiu perylene 41.01g, 7H-benzacridine 73.87g, potassium tert.-butoxide 17.06g, acid chloride (II) 0.72g, tri-tert phosphorus 0.81g, dissolved with 250ml toluene, in 88 ℃ of reactions 14 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains the two benzacridine compounds 005 of 56.67g white-yellowish solid, and productive rate is more than 83%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 682.81; Test value is 682.81.Ultimate analysis: calculated value is C:91.47%; H:4.43%; N:4.10%; Test value is C:91.48%; H:4.43%; N:4.11%.
Embodiment 6: compound 006 synthetic
Concrete synthetic route is as follows:
Take 3,6-, bis-bromine-N-phenylcarbazole 40.11g, 7H-benzacridine 76.04g, potassium tert.-butoxide 17.95g, acid chloride (II) 0.80g, tri-tert phosphorus 0.90g, dissolved with 250ml toluene, in 90 ℃ of reactions 15 hours.Filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, carries out recrystallization with toluene to the solid crude product obtaining, dry, obtains the two benzacridine compounds 006 of 55.92g white-yellowish solid, and productive rate is more than 83%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 673.80; Test value is 673.74.Ultimate analysis: calculated value is C:89.13%; H:4.64%; N:6.24%; Test value is C:89.14%; H:4.65%; N:6.21%.
Simultaneous test
We are mixed with respectively concentration by comparative sample 7H-benzacridine, the synthetic two benzacridine compounds 001-006 of embodiment of the present invention 1-6 is respectively 1 * 10
-6the solution of mol/L, is used Edinburdh-FLS920 equipment, and spin-coating method is made into film, has tested successively their luminous efficiency, and concrete data are as following table.
The luminous efficiency of table 1 couple benzacridine compounds 001-006 and comparative sample
| Compound | Luminous efficiency in dilute solution | Luminous efficiency in film |
| Comparative sample | 80% | 49% |
| 001 | 92% | 60% |
| 002 | 91% | 61% |
| 003 | 94% | 52% |
| 004 | 93% | 63% |
| 005 | 95% | 59% |
| 006 | 96% | 64% |
From the data of table 1, can find out, the luminous efficiency of 7H-benzacridine in dilute solution is 80%, and the luminous efficiency in film is 49%; And the luminous efficiency of two benzacridine compounds that the embodiment of the present invention is synthesized 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.
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 (2)
1. an electroluminescent organic material, is characterized in that, the concrete structure general formula of this material as the formula (1):
In formula, the concrete structure formula of A is as follows, the site that wherein * representative is connected with the nitrogen-atoms of benzacridine;
2. the preparation method of electroluminescent organic material according to claim 1, is characterized in that, this preparation method's concrete steps and condition are as follows:
For 1:3.0～3.5, take in molar ratio two bromo-derivatives and the 7H-benzacridine of A, with toluene, dissolve; Add again potassium tert.-butoxide, acid chloride, tri-tert phosphorus; Wherein the mol ratio of potassium tert.-butoxide and 7H-benzacridine is 0.40～0.45:1, and the mol ratio of acid chloride and 7H-benzacridine is 0.006～0.010:1, and the mol ratio of tri-tert phosphorus and 7H-benzacridine is 0.004～0.010:1;
Under nitrogen protection condition, by the mixing solutions of above-mentioned reactant, in temperature of reaction, be 80 ℃～90 ℃, react 10～15 hours; Cooling, filtering reacting solution, with the refining crude product obtaining of silica gel chromatography, then carry out recrystallization, obtain two benzacridine compounds after dry the crude product obtaining with toluene.
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Cited By (3)
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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 |
| CN105801569A (en) * | 2016-04-14 | 2016-07-27 | 中节能万润股份有限公司 | Organic photoelectric material and organic electroluminescent device containing material |
| WO2018138306A1 (en) * | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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