CN104629722A - Fluorene organic electroluminescent material and preparation method thereof - Google Patents
Fluorene 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, and aims to solve the technical problem that the luminescent efficiency of conventional luminescent materials cannot fulfill the requirements of OLED. The novel organic electroluminescent material is prepared by introducing substituents into a base material (indenofluorene compounds). By introducing different substituents, the provided material has a better planar structure and conjugate structure compared with common indenofluorene compounds, and the luminescent peaks can be adjusted by modulating the electron transition so as to obtain the required light-blue organic electroluminescent material. The luminescent efficiency of the provided material in a diluted solution is 96%, the luminescent efficiency in film is 83%, and the results show that the indenofluorene compounds have high luminescent efficiency. Compared with 5,5,10,10,15,15-hexaethyl-10,15-dihydro-5H-diindenofluorene, the provided preparation method of indenofluorene organic electroluminescent material has the advantages of simpler synthesis and purification, and lower cost, and is capable of fulfilling the industrial development requirements. The product yield is largely improved, the product purity is high, the HPLC purity is greater than 98%, the obtained material can prominently improve the efficiency, and the film-forming property and service life of the obtained material are both improved obviously.
Description
Technical field
The present invention relates to organic photoelectrical material field, be specifically related to a kind of indenofluorene class electroluminescent organic material and its preparation method and application.
Background technology
In numerous electroluminescent organic materials, compound containing indenofluorene structure is important integral part, indenofluorene compounds is the same with fluorenes, all there is the structure compared with rigidity, in addition, this compounds also has Heat stability is good, luminous efficiency advantages of higher, therefore, being that thermostability or fluorescence quantum efficiency are all better, is the desirable precursor of development of new OLED material.
Different three polyindenes are isomerss of three polyindenes, cause two compound phenyl ring directly mutual conjugation and name difference due to the difference of structure.Traditional synthetic method regulates loaded down with trivial details harshness, and yield is lower, limits its research and development and utilizes.
Within 2009, Yang Ji's water seminar of Taiwan Univ. reports novel starlike different trimerization indeno indenofluorene series derivates; With different three polyindenes that all alkyl replaces be core, the indenofluorene that replaces of aryl is for expanding conjugated structure unit.Research display: this compounds has beautiful and charming stability and blue light emitting performance, generally has higher fluorescence quantum efficiency (more than 70%) (J.-S. Yang, H.-H. Huang, Y.-H. Liu, S.-M. peng. Org., 2009,11,4942).
Indenofluorene micromolecular luminescent material has higher fluorescence quantum efficiency, and chemically modified is strong, is easy to purify, the advantages such as color gamut is wide.At present the research work of indenofluorene class luminescent material is mainly concentrated on, modify by carrying out replacement to indenofluorene, or indenofluorene derivative unit is introduced the approach such as macromolecular material to improve the luminescent properties of luminescent material.But existing indenofluorene micromolecular luminescent material still can not meet the requirement of OLED to work-ing life and luminous efficiency.
Summary of the invention
The present invention solves indenofluorene class luminescent material in prior art can not meet the technical problem of the service requirements of OLED, and it is simple to provide a kind of preparation method, luminous efficiency is high, indenofluorene class electroluminescent organic material that the life-span is long and its preparation method and application.
In order to solve the problems of the technologies described above, technical scheme of the present invention is specific as follows:
A kind of indenofluorene class electroluminescent organic material, the concrete structure general formula of this material as the formula (1):
Formula (1)
Wherein, A is independently selected from C
6-C
20phenyl, C
6-C
20substituted-phenyl, C
6-C
20aromatic heterocyclic radical, C
6-C
20the aromatic heterocyclic radical replaced.
Preferred compound of the present invention is: A is selected from 2-naphthyl, 2-anthryl, N-phenyl-2-carbazyl, triarylamine, 2-pyrenyl, 2-that thiazolinyl non-independently of one another.
Above-mentioned preferred indenofluorene class electroluminescent organic material of the present invention, concrete structural formula corresponds to the chemical structural formula of following 001-006 respectively:
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 based on structural formula (1), the arbitrary combination of the concrete structure provided before A group is respectively all should be included.
The preparation method of indenofluorene class electroluminescent organic material, concrete steps and the condition of this preparation method are as follows:
In molar ratio for 2:1 takes dimethyl formamide and phosphorus oxychloride, in molar ratio for 1:1 takes phosphorus oxychloride and 5,5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene.Ice-water bath reacts 1 hour, stirring at room temperature 1 hour, and 90 DEG C are stirred 2 hours, and adjust ph is within the scope of 6-8, through extraction, dry, rotate and steam, recrystallization, obtains 5, and 5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene-2,8,13-tri-aldehyde solid.
In molar ratio for 2:1 takes 4-bromobenzyl diethyl phosphoric acid and 5,5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene-2,8,13-tri-aldehyde, low-temp reaction 2 hours, room temperature reaction 2 hours.Through separatory, extraction, dry, concentrated, recrystallization, carries out drying under reduced pressure to the solid of gained, obtain, bromstyrol base indenofluorene analog derivative solid.
Take indenofluorene class bromine substituent for 1:4.0 ~ 6.5 in molar ratio and contain the substituent boric acid compound of A, by dissolution with solvents; Add sodium carbonate and solvent; The mol ratio of sodium carbonate and indenofluorene class bromine substituent is 3 ~ 4:1; Solvent is tetrahydrofuran (THF) and water; The volume ratio of tetrahydrofuran (THF) and water is 2:1.Degassed to reaction system; Add catalyzer four triphenyl phosphorus palladium, the mol ratio of four triphenyl phosphorus palladiums and indenofluorene class bromine substituent is 1:50 ~ 100; By the temperature of reaction system to 70-80 DEG C, react 24 ~ 30 hours; Cooling, suction filtration, washing, after drying, obtains described starlike indenofluorene analog derivative.
The invention has the beneficial effects as follows:
1, different three polyindene class electroluminescent organic materials provided by the invention are with based on 5,5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene, introduce double bond on this basis, a class new olefin class electroluminescent organic material of synthesis.The introducing of different substituents, making this material compare simple indenofluorene class has better two dimensional structure and conjugated system.The luminous efficiency of this material in dilute solution is 96%, and luminous efficiency is in the film 83%, shows that this indenofluorene compounds has high luminous efficiency.
2, the preparation method of indenofluorene class electroluminescent organic material provided by the invention, it synthesizes and purifies fairly simple, 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%.And the material prepared can the significantly improving of implementation efficiency, at film forming properties, the aspect in life-span is all significantly improved.
Embodiment
Indenofluorene class electroluminescent organic material provided by the invention is bromo-5,5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorenes of 2,8,13-tri-is raw material, and be obtained by reacting starlike indenofluorene analog derivative, its concrete synthetic route is as follows:
The synthetic method of bromo-5,5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorenes of 2,8,13-tri-:
In the there-necked flask having drying tube, add dry dimethyl formamide 6.2mL(0.08mol) and phosphorus oxychloride 3.8mL(0.04mol), ice-water bath stirs 1 hour, stirring at room temperature 1 hour.Add 5,5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene 10g(0.04mol) and dimethyl formamide 20mL, mixture stirs 2 hours at 90 DEG C, suitably after cooling, add trash ice or cold water 5g, under violent stirring condition, first add the sodium hydroxide solution that massfraction is 40%, then add in saturated acetic acid sodium solution, regulate pH within the scope of 6-8, finally use chloroform extraction.The a large amount of salt solution continuous flushing of extract, anhydrous magnesium sulfate drying, spends the night, and rotary evaporation is drained, re-crystallizing in ethyl acetate, obtains the micro-yellow solid of 5,5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene-2,8,13-tri-aldehyde 50.56g.
Under nitrogen protection condition, add 4-bromobenzyl diethyl phosphoric acid 104.42g and tetrahydrofuran (THF) 100ml, after being cooled to-65 DEG C; add potassium tert.-butoxide 50.00g, after low temperature stirs 3 hours, in reaction solution, drip 5; 5,10,10; 15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene-2; the tetrahydrofuran solution 180ml of 8,13-tri-aldehyde, reacts 2 hours; warming while stirring, to room temperature, continues reaction 2 hours.To in the reaction solution of gained, add separatory after distilled water, toluene, form water layer and organic layer.After extracting this water layer with toluene, this toluene and organic layer are merged, clean with saturated aqueous common salt, with anhydrous sodium sulfate drying, concentrated, with re crystallization from toluene, carry out drying under reduced pressure to the solid of gained, result obtains the white-yellowish solid bromstyrol base indenofluorene analog derivative luminous organic material of 80.09g.HPLC purity is greater than 98%.
Embodiment 1: the synthesis of compound 001
Concrete synthetic route is shown below:
By bromstyrol base indenofluorene analog derivative 10.54g(10mmol), 2-naphthalene boronic acids 6.88g(40mmol), sodium carbonate 3.18g(30mmol), tetrahydrofuran (THF) 200ml and water 100ml adds there-necked flask, degassed, add four triphenyl phosphorus palladium 0.12g(0.10mmol), be warming up to 70 DEG C, react 24 hours, be cooled to room temperature, after separating out solid, suction filtration, filter cake, after washing, ethanol are washed and washed with ether, is dried and is obtained starlike indenofluorene olefines derivative 8.96g, productive rate more than 75%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1195.61; Test value is 1195.62.Ultimate analysis: calculated value is C:93.42%; H:6.58%; Test value is C:93.41%; H:6.59%.
Embodiment 2: the synthesis of compound 002
Concrete synthetic route is shown below:
By bromstyrol base indenofluorene analog derivative 10.54g(10mmol), 2-pyrenyl boric acid 11.07g(45mmol), sodium carbonate 3.39g(32mmol), tetrahydrofuran (THF) 200ml and water 100ml adds there-necked flask, degassed, add four triphenyl phosphorus palladium 0.14g(0.12mmol), be warming up to 72 DEG C, react 25 hours, be cooled to room temperature, after separating out solid, suction filtration, filter cake, after washing, ethanol are washed and washed with ether, is dried and is obtained starlike indenofluorene olefines derivative 10.77g, productive rate more than 76%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1417.85; Test value is 1417.83.Ultimate analysis: calculated value is C:94.03%; H:5.97%; Test value is C:94.04%; H:5.96%.
Embodiment 3: the synthesis of compound 003
Concrete synthetic route is shown below:
By bromstyrol base indenofluorene analog derivative 10.54g(10mmol), N-phenyl carbazole ylboronic acid 14.35g(50mmol), sodium carbonate 3.60g(34mmol), tetrahydrofuran (THF) 200ml and water 100ml adds there-necked flask, degassed, add four triphenyl phosphorus palladium 0.16g(0.14mmol), be warming up to 74 DEG C, react 26 hours, be cooled to room temperature, after separating out solid, suction filtration, filter cake, after washing, ethanol are washed and washed with ether, is dried and is obtained starlike indenofluorene olefines derivative 11.56g, productive rate more than 75%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1541.01; Test value is 1541.03.Ultimate analysis: calculated value is C:91.19%; H:6.08%; N:2.73%; Test value is C:91.18%; H:6.09%; N:2.73%.
Embodiment 4: the synthesis of compound 004
Concrete synthetic route is shown below:
By bromstyrol base indenofluorene analog derivative 10.54g(10mmol), 2-anthryl boric acid 12.21g(55mmol), sodium carbonate 3.81g(36mmol), tetrahydrofuran (THF) 200ml and water 100ml adds there-necked flask, degassed, add four triphenyl phosphorus palladium 0.18g(0.16mmol), be warming up to 76 DEG C, react 27 hours, be cooled to room temperature, after separating out solid, suction filtration, filter cake, after washing, ethanol are washed and washed with ether, is dried and is obtained starlike indenofluorene olefines derivative 10.22g, productive rate more than 76%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1345.79; Test value is 1345.78.Ultimate analysis: calculated value is C:93.71%; H:6.29%; Test value is C:93.73%; H:6.27%.
Embodiment 5: the synthesis of compound 005
Concrete synthetic route is shown below:
By bromstyrol base indenofluorene analog derivative 10.54g(10mmol), 2-that ene boric acid non-12.60g(60mmol), sodium carbonate 4.02g(38mmol), tetrahydrofuran (THF) 200ml and water 100ml adds there-necked flask, degassed, add four triphenyl phosphorus palladium 0.20g(0.18mmol), be warming up to 78 DEG C, react 28 hours, be cooled to room temperature, after separating out solid, suction filtration, filter cake, after washing, ethanol are washed and washed with ether, is dried and is obtained starlike indenofluorene olefines derivative 10.34g, productive rate more than 79%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1309.76; Test value is 1309.75.Ultimate analysis: calculated value is C:93.54%; H:6.46%; Test value is C:93.55%; H:6.45%.
Embodiment 6: the synthesis of compound 006
Concrete synthetic route is shown below:
By bromstyrol base indenofluorene analog derivative 10.54g(10mmol), 4-(diphenyl amino) phenyl-boron dihydroxide 18.79g(65mmol), sodium carbonate 4.23g(40mmol), tetrahydrofuran (THF) 200ml and water 100ml adds there-necked flask, degassed, add four triphenyl phosphorus palladium 0.23g(0.20mmol), be warming up to 80 DEG C, react 30 hours, be cooled to room temperature, after separating out solid, suction filtration, filter cake, after washing, ethanol are washed and washed with ether, is dried and is obtained starlike indenofluorene olefines derivative 12.06g, productive rate more than 78%, HPLC purity is greater than 98%.Mass spectrum: calculated value is 1547.06; Test value is 1547.04.Ultimate analysis: calculated value is C:90.83%; H:6.45%; N:2.72%; Test value is C:90.82%; H:6.46%; N:2.70%.
application implementation case
It is 1 × 10 that comparative sample 5,5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene (S), product 001-006 are mixed with concentration by respectively
-6the solution of mol/L, use Edinburdh-FLS920 equipment, spin-coating method is made into film, tests their luminous efficiency respectively, and concrete data are as following table.
The luminous efficiency of gained compound in table 1 embodiment
As can be seen from the data of table 1, target product 001-006 compares with comparative sample, and the luminous efficiency in dilute solution, the luminous efficiency in film are all significantly improved.Compared by data, we find that this kind of material is the electroluminescent organic material of excellent property, are very promising class electroluminescent organic materials.
Should be understood that, application of the present invention is not limited to above-mentioned citing, for those of ordinary skills, can be improved according to the above description or convert, and all these improve and convert the protection domain that all should belong to 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):
Formula (1)
In formula, A is independently selected from C
6-C
20phenyl, C
6-C
20substituted-phenyl, C
6-C
20aromatic heterocyclic radical, C
6-C
20the aromatic heterocyclic radical replaced.
2. electroluminescent organic material according to claim 1, is characterized in that, A is selected from 2-naphthyl, 2-anthryl, N-phenyl-2-carbazyl, triarylamine, 2-pyrenyl, 2-that thiazolinyl non-independently of one another.
3. the preparation method of electroluminescent organic material according to claim 1 and 2, is characterized in that, concrete steps and the condition of this preparation method are as follows:
(1) in molar ratio for 2:1 takes dimethyl formamide and phosphorus oxychloride, in molar ratio for 1:1 takes phosphorus oxychloride and 5,5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene; Ice-water bath reacts 1 hour, stirring at room temperature 1 hour, and 90 DEG C are stirred 2 hours, and adjust ph is within the scope of 6-8, through extraction, dry, rotate and steam, recrystallization, obtains 5, and 5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene-2,8,13-tri-aldehyde solid;
(2) in molar ratio for 2:1 takes 4-bromobenzyl diethyl phosphoric acid and 5,5,10,10,15,15-Hexaethyl-10,15-dihydro-5H-two indenofluorene-2,8,13-tri-aldehyde, low-temp reaction 2 hours, room temperature reaction 2 hours; Through separatory, extraction, dry, concentrated, recrystallization, carries out drying under reduced pressure to the solid of gained, obtain, bromstyrol base indenofluorene analog derivative solid;
(3) take indenofluorene class bromine substituent for 1:4.0 ~ 6.5 in molar ratio and contain the substituent boric acid compound of A, by dissolution with solvents; Add sodium carbonate and solvent; The mol ratio of sodium carbonate and indenofluorene class bromine substituent is 3 ~ 4:1; Solvent is tetrahydrofuran (THF) and water; The volume ratio of tetrahydrofuran (THF) and water is 2:1; Degassed to reaction system; Add catalyzer four triphenyl phosphorus palladium, the mol ratio of four triphenyl phosphorus palladiums and indenofluorene class bromine substituent is 1:50 ~ 100; By the temperature of reaction system to 70-80 DEG C, react 24 ~ 30 hours; Cooling, suction filtration, washing, after drying, obtains described starlike indenofluorene analog derivative.
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| CN108558595A (en) * | 2018-05-22 | 2018-09-21 | 南京林业大学 | A kind of phenylenevinylene's bridging trimer indene derivative and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108558595A (en) * | 2018-05-22 | 2018-09-21 | 南京林业大学 | A kind of phenylenevinylene's bridging trimer indene derivative and preparation method thereof |
| CN108558595B (en) * | 2018-05-22 | 2021-02-02 | 南京林业大学 | P-phenylene ethylene bridged trimer indene derivative and preparation method thereof |
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