CN101864295A - Small molecular blue light material and preparation method thereof - Google Patents
Small molecular blue light material and preparation method thereof Download PDFInfo
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- CN101864295A CN101864295A CN201010210981A CN201010210981A CN101864295A CN 101864295 A CN101864295 A CN 101864295A CN 201010210981 A CN201010210981 A CN 201010210981A CN 201010210981 A CN201010210981 A CN 201010210981A CN 101864295 A CN101864295 A CN 101864295A
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Abstract
The invention discloses a small molecular blue light material and a preparation method thereof. The preparation method is characterized by adopting the following three-step reaction of: (1) preparing 2,3,6,7-tetra-tertiary butyl-octahydro-anthraquinone; (2) preparing 2,3,6,7-tetra-tertiary butyl anthraquinone; and (3) preparing 2,3,6,7-tetra-tertiary butyl-9,10-(1-dinaphthyl)-anthracene. The four tertiary butyls in the synthesized blue light material reduce the fluorescence quenching effect at higher doping concentration to a greater degree, and the luminous efficiency is improved. Moreover, the 2,3,6,7-tetra-tertiary butyl-9,10-(1-dinaphthyl)-anthracene introduces four tertiary butyls, and material molecules increase steric hindrance on an anthracene framework of a planar structure so as to prevent aggregation between molecular chromophores more effectively, reduce interaction between molecules and remarkably improve the luminous performance of the material.
Description
Technical field:
The invention belongs to the electroluminescent organic material technical field, relate in particular to a kind of preparation method of small molecular blue light material.
Background technology:
Along with the continuous development of information technology, luminescent material is in the application of information demonstration, optical communication and other optoelectronic areas people's attention extremely, and luminescent material and device that people are making great efforts development of new are used for flat pannel display.In recent years, a kind of novel organic electroluminescent flat-panel screens (OLED) has been subjected to people's extensive concern.Compare with liquid crystal flat panel display, the organic electroluminescent flat-panel screens has distinguishing features such as active illuminating, light, thin, good contrast, non-angular dependency, energy consumption are low, has broad application prospects.OLED has proposed to comprise that red, green, blue three primary colours method, white light add multiple schemes such as colour filter embrane method, blue light energy transformation method aspect the colorize of device, and has many companies to release the OLED product that full color shows.
In the OLED display device, the stability problem that is used as the electroluminescent material of luminescent layer is a urgent problem.The small molecules organic compound is because easily crystallization, thereby forms stain after making device easily in film, thereby reduces the life-span of device.Thereby the luminescent material that exploitation can have higher thermostability and spectrum stability is one of emphasis direction of present electroluminescent organic material research.
Summary of the invention:
The objective of the invention is to overcome the low thermostability of existing electroluminescent material and the shortcoming of spectrum stability, a kind of small molecular blue light material (2 with high thermal stability and spectrum stability is provided, 3,6,7-tetra-tert-9,10-(1-dinaphthyl)-anthracene) synthetic method adopts synthetic luminous organic material of the present invention can realize blue emission.
The objective of the invention is to realize by following steps:
A kind of small molecular blue light material, described small molecular blue light material is 2,3,6,7-tetra-tert-9,10-(1-dinaphthyl)-anthracene, its molecular structure is:
The emission peak of described small molecular blue light material is 470nm, and the CIE coordinate is (0.16,0.21), and current efficiency is 5.4cd/A.
The preparation method of described a kind of small molecular blue light material, according to following steps:
(1) preparation 2,3,6,7-tetra-tert-octahydro-anthraquinone;
(2) preparation 2,3,6,7-tetra-tert anthraquinone;
(3) preparation 2,3,6,7-tetra-tert-9,10-(1-dinaphthyl)-anthracene.
Described step (1) is meant: in the there-necked flask of the 500ml that is furnished with reflux condensing tube, add 20g para benzoquinone, 30g 2 successively, and the toluene solvant of 3-di-t-butyl-1,3-butadiene and 200ml, heating reflux reaction obtained mixing solutions in 24～48 hours; After mixing solutions was cooled to room temperature, under stirring condition, to wherein adding 1000ml ethanol, suction filtration got white solid, and white solid is carried out recrystallization with toluene, product 2,3,6,7-tetra-tert-octahydro-anthraquinone, productive rate are 80%.
Described step (2) is meant: in the there-necked flask of the 500ml that is furnished with reflux condensing tube and airway, add 20g2 successively, 3,6, the potassium hydroxide-ethanol solution 350ml of 7-tetra-tert-octahydro-anthraquinone and mass percent concentration 3～8%, feed high purity oxygen gas then and stir in there-necked flask, react after 24～48 hours, suction filtration gets product 2,3,6,7-tetra-tert anthraquinone, productive rate are 95%.
Described step (3) is meant: have in the there-necked flask of reflux condensing tube and airway at 500ml, add the 80ml anhydrous diethyl ether, under logical nitrogen protection, add the 1-bromonaphthalene of 0.45g lithium and 6ml, heating reflux reaction obtained once mixture in 2～3 hours; Add 80ml 2,3,6 in above-mentioned once mixture, the toluene solution of 7-tetra-tert anthraquinone obtains secondary mixture, and wherein 2,3,6, the toluene solution of 7-tetra-tert anthraquinone contains 4g 2,3,6,7-tetra-tert anthraquinone; Under the nitrogen protection atmosphere, heating reflux reaction added mixture of ice and water after 12～24 hours when the question response system is reduced to room temperature, fully stir; hydrolysis reaction is evenly carried out, and suction filtration gets product 2,3,6; 7-tetra-tert-9,10-(1-dinaphthyl)-anthracene, productive rate is 98%.
Fluorescence quenching when four tertiary butyls in the synthetic blue light material molecule of the present invention have reduced higher-doped concentration largely, luminous efficiency is improved, in addition, 2,3,6,7-tetra-tert-9,10-(1-dinaphthyl)-anthracene has been introduced four tertiary butyls in molecular skeleton, material molecule has increased sterically hindered on the anthracene skeleton of two dimensional structure, can more effectively stop the gathering between the molecule chromophoric group, reduce intermolecular interaction, thereby the material luminescent properties is significantly improved.
Description of drawings:
Fig. 1: 2,3,6,7-tetra-tert-9, the electroluminescent spectrum figure of 10-(1-dinaphthyl)-anthracene;
Wherein: as can be seen from Figure 1, the peak value 470nm of the electroluminescent spectrum of this material.
Embodiment:
Below in conjunction with accompanying drawing the present invention is done and to describe in further detail:
Embodiment 1
In the there-necked flask of the 500mL that is furnished with reflux condensing tube, add 20 gram para benzoquinone, 30 grams 2 successively, 3-di-t-butyl-1, the toluene solvant of 3-divinyl and 200mL, heating reflux reaction 24-48 hour, after reaction system is cooled to room temperature, 1000mL ethanol is joined in the above-mentioned reaction system under stirring condition, and suction filtration gets white solid.Products therefrom is carried out recrystallization with an amount of toluene get product 2,3,6,7-tetra-tert-octahydro-anthraquinone, productive rate 80%;
In the there-necked flask of the 500mL that is furnished with reflux condensing tube and airway, add 20 grams 2 successively, 3,6, the potassium hydroxide-ethanol solution of 7-tetra-tert-octahydro-anthraquinone and 350mL (mass concentration 3-8%) fed the high purity oxygen gas stirring reaction 24-48 hour in there-necked flask, reaction finishes the back suction filtration and gets product 2,3,6,7-tetra-tert anthraquinone, productive rate are 95%
Have at 500mL and to add the 80mL anhydrous diethyl ether in the there-necked flask of reflux condensing tube and airway; the 1-bromonaphthalene that under logical nitrogen protection, adds 0.45g lithium and 6mL; heating reflux reaction 2-3 hour; add 80mL 2,3 then, 6; the toluene solution of 7-tetra-tert anthraquinone (contains 4g2; 3,6,7-tetra-tert anthraquinone).After heating reflux reaction 12-24 under the nitrogen protection atmosphere hour, the question response system adds a large amount of mixture of ice and water when reducing to room temperature, fully stirs hydrolysis reaction is evenly carried out.Suction filtration gets product 2,3,6,7-tetra-tert-9, and 10-(1-dinaphthyl)-anthracene, productive rate is 98%.
Adopt synthetic 2,3,6 of the present invention, 7-tetra-tert-9, the OLED display device that 10-(1-dinaphthyl)-anthracene is made can send blue light, and its electroluminescent spectrum figure sees accompanying drawing 1, and its emission peak is 470nm, the CIE coordinate is (0.16,0.21), and current efficiency is 5.4cd/A.
Above content is to further describing that the present invention did in conjunction with concrete preferred implementation; can not assert that the specific embodiment of the present invention only limits to this; for the general technical staff of the technical field of the invention; without departing from the inventive concept of the premise; can also make some simple deduction or replace, all should be considered as belonging to the present invention and determine scope of patent protection by claims of being submitted to.
Claims (6)
1. small molecular blue light material, it is characterized in that: described small molecular blue light material is 2,3,6,7-tetra-tert-9,10-(1-dinaphthyl)-anthracene, its molecular structure is:
2. a kind of according to claim 1 small molecular blue light material is characterized in that: the emission peak of described small molecular blue light material is 470nm, and the CIE coordinate is (0.16,0.21), and current efficiency is 5.4cd/A.
3. a kind of preparation method of small molecular blue light material as claimed in claim 1 or 2 is characterized in that, according to following steps:
(1) preparation 2,3,6,7-tetra-tert-octahydro-anthraquinone;
(2) preparation 2,3,6,7-tetra-tert anthraquinone;
(3) preparation 2,3,6,7-tetra-tert-9,10-(1-dinaphthyl)-anthracene.
4. as the preparation method of a kind of small molecular blue light material as described in the claim 3, it is characterized in that, described step (1) is meant: add 20g para benzoquinone, 30g 2 in the there-necked flask of the 500ml that is furnished with reflux condensing tube successively, 3-di-t-butyl-1, the toluene solvant of 3-divinyl and 200ml, heating reflux reaction obtained mixing solutions in 24～48 hours; After mixing solutions was cooled to room temperature, under stirring condition, to wherein adding 1000ml ethanol, suction filtration got white solid, and white solid is carried out recrystallization with toluene, product 2,3,6,7-tetra-tert-octahydro-anthraquinone, productive rate are 80%.
5. as the preparation method of a kind of small molecular blue light material as described in the claim 3, it is characterized in that described step (2) is meant: in the there-necked flask of the 500ml that is furnished with reflux condensing tube and airway, add 20g 2,3 successively, 6, the potassium hydroxide-ethanol solution 350ml of 7-tetra-tert-octahydro-anthraquinone and mass percent concentration 3～8%, feed high purity oxygen gas then and stir in there-necked flask, react after 24～48 hours, suction filtration gets product 2,3,6,7-tetra-tert anthraquinone, productive rate are 95%.
6. as the preparation method of a kind of small molecular blue light material as described in the claim 3, it is characterized in that, described step (3) is meant: have in the there-necked flask of reflux condensing tube and airway at 500ml, add the 80ml anhydrous diethyl ether, under logical nitrogen protection, add the 1-bromonaphthalene of 0.45g lithium and 6ml, heating reflux reaction obtained once mixture in 2～3 hours; Add 80ml 2,3,6 in above-mentioned once mixture, the toluene solution of 7-tetra-tert anthraquinone obtains secondary mixture, and wherein 2,3,6, the toluene solution of 7-tetra-tert anthraquinone contains 4g 2,3,6,7-tetra-tert anthraquinone; Under the nitrogen protection atmosphere, heating reflux reaction added mixture of ice and water after 12～24 hours when the question response system is reduced to room temperature, fully stir; hydrolysis reaction is evenly carried out, and suction filtration gets product 2,3,6; 7-tetra-tert-9,10-(1-dinaphthyl)-anthracene, productive rate is 98%.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110283064A (en) * | 2019-06-17 | 2019-09-27 | 武汉依麦德新材料科技有限责任公司 | A kind of 9,10- anthraquinone derivative and its preparation method and application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101698796A (en) * | 2008-11-24 | 2010-04-28 | 上海拓引数码技术有限公司 | Substituted 9,10-dinaphthyl anthracene blue light-emitting organic electro-luminescent material and method for preparing same |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101698796A (en) * | 2008-11-24 | 2010-04-28 | 上海拓引数码技术有限公司 | Substituted 9,10-dinaphthyl anthracene blue light-emitting organic electro-luminescent material and method for preparing same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110283064A (en) * | 2019-06-17 | 2019-09-27 | 武汉依麦德新材料科技有限责任公司 | A kind of 9,10- anthraquinone derivative and its preparation method and application |
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