CN106957264A - A kind of fluorenes spiral shell dibenzo acridine class electroluminescent organic material and its application - Google Patents
A kind of fluorenes spiral shell dibenzo acridine class electroluminescent organic material and its application Download PDFInfo
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- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The present invention relates to a kind of fluorenes spiral shell dibenzo acridine class electroluminescent organic material and its application, with the molecular structure as shown in formula I：Wherein, Ar1、Ar2Independently selected from hydrogen or aromatic group.The electroluminescent organic material of the present invention, with good film forming, suitable molecular entergy level, such luminous organic material can change electron transition due to the introducing of different substituents, its luminous peak position is adjusted, is a kind of good luminescent material of luminous efficiency.
Description
Technical field
Sent out the present invention relates to a kind of electroluminescent organic material, more particularly to a kind of fluorenes spiral shell dibenzo acridine class organic electroluminescence
Luminescent material and its application.
Background technology
In recent years, organic electroluminescent LED (Organic Light-Emitting Diodes, abbreviation OLEDs) is made
The visual field of people is progressed into for a kind of new and promising Display Technique.OLEDs has self-luminous, driving voltage low, light
Thin, luminous visual angle is wide, fast response time, flexible folding, energy consumption is low, the advantages of can carry out large area production.At present, Organic Electricity
Photoluminescence technology, is mainly used in two fields, respectively full-color display and white-light illuminating, based on OLED Display Techniques
Commodity, have been done step-by-step industrialization, such as, and in the commodity such as smart mobile phone, curved surface TV, this is applied widely
Item technology.In order to realize full-color display, display panel needs the display unit with three kinds of colors of red, green, blue.At small point
In sub- OLED, relative to red device and green device, the development of blue-light device is still not mature enough, the colour purity of blue-light device
Degree, efficiency and life-span all have much room for improvement.
Acridan and its derivative have good hole transport performance, are widely used to OLED material synthesis neck
Domain.Spirane structure has cross one another space structure, can be prevented effectively from molecule aggregation, increase thin film stability；Rigid spiral shell
Ring knot can effectively improve the heat endurance of material；Different substituents are introduced by the avtive spot in spirane structure, can effectively be adjusted
The emission wavelength of material is saved, improves the excitation of material, obtains the electroluminescent organic material of function admirable.
The content of the invention
There is provided a kind of fluorenes spiral shell dibenzo acridine class organic electroluminescent for deficiency of the invention for the presence of existing blue-light device
Material and its application.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：
A kind of fluorenes spiral shell dibenzo acridine class electroluminescent organic material, it is characterised in that it has the molecule as shown in formula I
Structure：
Wherein, Ar1、Ar2Independently selected from hydrogen or aromatic group.
Further, the Ar1、Ar2Any one in following radicals：
Wherein E represents chemical bond connection site.
Further, the electroluminescent organic material its there is molecular structure as shown in A1-A33：
The beneficial effect for the electroluminescent organic material that the present invention is provided is：
1) spirane structure is included in molecular structure, spirane structure has larger dihedral angle, can effectively reduce intermolecular has
Sequence accumulation caused by fluorescent quenching, the molecular rigidity feature of spirane structure, can effectively improve molecule glass transition temperature and
Heat decomposition temperature, the stability of electroluminescent organic material is high, has great benefit to the life-span for further improving device.
2) electroluminescent organic material of the invention, with good film forming, suitable molecular entergy level, such organic hair
Luminescent material can change electron transition due to the introducing of different substituents, adjust its luminous peak position, be a kind of luminous effect
The good luminescent material of rate.
3) luminescent device prepared by the electroluminescent organic material provided using the present invention has heat endurance good, excitation
Good advantage.
The synthetic route for the electroluminescent organic material that the present invention is provided is as follows：
(1) preparation of intermediate A：2- bromo biphenyls are reacted with n-BuLi, raw material F successively, then through being dehydrated cyclization reaction
Intermediate A is obtained, reaction equation is as follows：
The preparation of intermediate B：2- bromo biphenyls are reacted with n-BuLi, raw material G successively, then is obtained through being dehydrated cyclization reaction
Intermediate B, reaction equation is as follows：
(2) intermediate A or B are coupled through C-C or C-N couplings obtains the electroluminescent organic material, reaction equation is as follows：
The organic electroluminescence device for containing above-mentioned electroluminescent organic material in functional layer is also claimed in the present invention.
Further, the functional layer refers to luminescent layer.
Further, its structure includes indium tin oxide-coated glass substrate, the hole being sequentially overlapped from below to up
Transport layer, luminescent layer, electron transfer layer, electron injecting layer and cathode layer.
The beneficial effect for the organic electroluminescence device that the present invention is provided is：It is prepared by the electroluminescent organic material of the present invention
Method is simple, can be as blue emitting material with suitable molecular entergy level, and material heat endurance is good, high color purity.
Embodiment
The principle and feature of the present invention are described below in conjunction with example, the given examples are served only to explain the present invention, and
It is non-to be used to limit the scope of the present invention.
First, the preparation method of electroluminescent organic material
Embodiment 1：The preparation of intermediate A, intermediate B
1st, the preparation of intermediate A, reaction scheme is as follows：
Specifically course of reaction is：Under nitrogen protection, added in 250mL there-necked flasks 2- bromo biphenyls (2.56g,
11.0mmol) and 40mL tetrahydrofurans, be placed in low temperature bath and be cooled to -78 DEG C, be added dropwise n-BuLi (0.7g,
11.0mmol), -78 DEG C are reacted 2 hours, and raw material F (4.5g, 10.0mmol) is dissolved in into 70mL tetrahydrofurans and instilled above-mentioned anti-
System is answered, -78 DEG C are reacted 2 hours.Warm naturally to add the quenching reaction of 30mL 15% (wt%) watery hydrochloric acid after 0~5 DEG C, point
Liquid, removing solvent obtain 5.44g intermediate A -1, yield 90%.A-1 (5.44g, 8.77mmol) is added into 250mL there-necked flasks
In, and add 120mL acetic acid and 0.5mL 36% (wt%) concentrated hydrochloric acid, 110 DEG C of back flow reactions 3.5 hours are naturally cooling to 20-
25 DEG C, product is separated out, suction filtration, collects filter cake, and crude product toluene crystallization obtains 4.37g intermediate As, yield 85%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C39H24BrN, theoretical value 585.109, test value
585.110.Elementary analysis (C39H24BrN), theoretical value C：79.86, H：4.12, Br：13.62, N：2.39, measured value C：
79.87, H：4.11, Br：13.62, N：2.39.
2nd, the preparation of intermediate B, reaction scheme is as follows：
Specific preparation process refers to the preparation process of intermediate A.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C39H23Br2N, theoretical value 663.020, test value
663.021.Elementary analysis (C39H23Br2N), theoretical value C：70.39, H：3.48, Br：24.02, N：2.10, measured value C：
70.39, H：3.48, Br：24.02, O：2.10.
Embodiment 2：Compound A1 preparation
Reaction scheme is as follows:
Specific course of reaction is with the preparation process of intermediate A, yield 86.8%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C39H25N, theoretical value 507.119, test value
507.120.Elementary analysis (C39H25N), theoretical value C：92.28, H：7.96, N：2.76, measured value C：92.28, H：7.97, N：
7.75。
Embodiment 3：The preparation of compound A-13
Reaction scheme is as follows：
Specifically course of reaction is：Under nitrogen protection, by intermediate A (1.47g, 2.5mmol), raw material A 3-1 (0.41g,
2.5mmol), 80mL toluene and 20mL water are added in 250mL there-necked flasks, then put into catalyst tetrakis triphenylphosphine palladium
(0.029g, 0.025mmol), acid binding agent potassium carbonate (0.69g, 5.0mmol).System is warming up to back flow reaction 8 hours, natural
20~25 DEG C are cooled to, point liquid removes solvent, by crude product toluene crystallization, obtains 1.22g object A3, yield 78.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C48H35N, theoretical value 625.277, test value
625.277.Elementary analysis (C48H35N), theoretical value C：92.12, H：5.64, N：2.24, measured value C：92.12, H：5.64, N：
2.24。
Embodiment 4：Compound A11 preparation
Reaction scheme is as follows：
Specific course of reaction replaces with raw material A 3-1 (0.41g, 2.5mmol) with reference to the course of reaction of embodiment 3
A11-1 (0.50g, 2.5mmol), total recovery 78.6%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C51H33N, theoretical value 659.261, test value
659.260.Elementary analysis (C51H33N), theoretical value C：92.84, H：5.04, N：2.12, measured value C：92.83, H：5.05, N：
2.12。
Embodiment 5：Compound A13 preparation
Reaction scheme is as follows：
Specifically course of reaction is：Under nitrogen protection, by intermediate B (1.33g, 2.0mmo l), raw material A 13-1
(0.37g, 2.2mmol) and 120mL toluene are added in 250mL there-necked flasks, then put into catalyst acetic acid palladium (0.011g,
0.05mmol), catalyst ligand tri-butyl phosphine tetrafluoroborate (0.026g, 0.1mmol), acid binding agent sodium tert-butoxide
(0.38g, 4mmol).System is warming up to back flow reaction 8 hours, is naturally cooling to add 50mL water quenchings after 20~25 DEG C and goes out reaction,
Divide liquid, remove solvent, by crude product toluene crystallization, obtain 1.33g object A13, yield 79.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C63H43N3, theoretical value 841.346, test value 841.345.
Elementary analysis (C63H43N3), theoretical value C：89.86, H：5.15, N：4.99, measured value C：89.86, H：5.15, N：4.99.
Embodiment 6：Compound A19 preparation：
Reaction scheme is as follows：
Specific course of reaction with reference to embodiment 5 course of reaction, by raw material A 13-1 replace with A19-1 (0.37g,
2.2mmol), total recovery 76.8%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C50H33N3, theoretical value 675.267, test value 675.266.
Elementary analysis (C50H33N3), theoretical value C：88.86, H：4.92, N：6.22, measured value C：88.86, H：4.91, N：6.23.
Embodiment 7：Compound A28 preparation
Reaction scheme is as follows：
Specific course of reaction replaces A3-1 (0.41g, 2.5mmol) with reference to the course of reaction of the compound A-13 of embodiment 3
For A28-1 (0.72g, 2.5mmol), total recovery 77.6%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C57H36N2, theoretical value 748.288, test value 748.287.
Elementary analysis (C57H36N2), theoretical value C：91.41, H：4.85, N：3.74, measured value C：91.41, H：4.85, N：3.74.
2nd, organic electroluminescence device
We choose compound A1, compound A-13, compound A11, compound A13, compound A19, compound A28 conducts
Luminescent layer makes organic electroluminescence device.The structure for the organic electroluminescence device that we make sequentially consists of ITO
Conducting Glass, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode layer.It should be appreciated that device is real
Process and result are applied, is intended merely to preferably explain the present invention, not limitation of the present invention.
Organic electroluminescence device preparation method used in the present embodiment is as follows：
A) ITO (tin indium oxide) glass is cleaned：Ito glass each 30 is cleaned with deionized water, acetone, EtOH Sonicate respectively
Minute, then handled 5 minutes in plasma cleaner；
B) vacuum evaporation hole transmission layer (NPB) successively on anode ito glass, thickness is 50nm；, evaporation rate
0.1nm/s；
C) the luminescent layer compound that the vacuum evaporation present invention is provided on hole transmission layer (NPB), thickness is 30nm, is steamed
Plating speed is 0.1nm/s；
D) vacuum evaporation is as the TPBI of electron transfer layer on luminescent layer, and thickness is 30nm；
E) on electron transfer layer, vacuum evaporation electron injecting layer LiF, thickness is 1nm；
F) on electron injecting layer, vacuum evaporation negative electrode Al, thickness is 100nm.
In order to verify the performance for the organic electroluminescence device that the present invention is provided, we are to compound A1, compound A-13, change
Organic electroluminescence device one that compound A11, compound A13, compound A19, compound A28 make as luminescent layer, device
2nd, device three, device four, device five, device six have carried out performance test, as a result as shown in table 1.
The device photoelectric tables of data of table 1
The organic electroluminescence device chromaticity coordinate that the present invention is provided it can be seen from the data in table 1 is (0.15-
0.17,0.09-0.15), it is a preferable blue luminescent device of class excitation, the high-high brightness 1020-3930cd/m of device2,
Maximum current efficiency is 1.1-1.6cd/A, and device efficiency is good, is a kind of blue-light device of function admirable.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and
Within principle, any modifications, equivalent substitutions and improvements made etc. should be included within the scope of the present invention.
Claims (6)
1. a kind of fluorenes spiral shell dibenzo acridine class electroluminescent organic material, it is characterised in that it has the molecule knot as shown in formula I
Structure：
Wherein, Ar1、Ar2Independently selected from hydrogen or aromatic group.
2. electroluminescent organic material according to claim 1, it is characterised in that the Ar1、Ar2Independently selected from following
Any one in group：
Wherein E represents chemical bond connection site.
3. electroluminescent organic material according to claim 1 or 2, it is characterised in that it has as shown in A1-A33
Molecular structure：
4. a kind of organic electroluminescence device, it is characterised in that included in the functional layer of the luminescent device in claim 1-3
Electroluminescent organic material described in any one.
5. organic electroluminescence device according to claim 4, it is characterised in that the functional layer refers to luminescent layer.
6. organic electroluminescence device according to claim 5, it is characterised in that its structure includes folding successively from below to up
Plus indium tin oxide-coated glass substrate, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode layer.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109574858A (en) * | 2017-09-28 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of spiral shell dimethylanthracene fluorenes class organic compound and its application on organic electroluminescence device |
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| CN101659638A (en) * | 2008-08-26 | 2010-03-03 | 财团法人工业技术研究院 | Organic compound and organic electroluminescent device containing same |
| CN104892578A (en) * | 2015-05-19 | 2015-09-09 | 苏州大学 | Triphenylamine spirofluorene derivatives and uses thereof |
| CN105238389A (en) * | 2015-10-12 | 2016-01-13 | 中节能万润股份有限公司 | Novel organic electroluminescent material and use thereof |
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| US20100019658A1 (en) * | 2008-07-22 | 2010-01-28 | Industrial Technology Research Institute | Organic compound and organic electroluminescence device employing the same |
| CN101659638A (en) * | 2008-08-26 | 2010-03-03 | 财团法人工业技术研究院 | Organic compound and organic electroluminescent device containing same |
| CN104892578A (en) * | 2015-05-19 | 2015-09-09 | 苏州大学 | Triphenylamine spirofluorene derivatives and uses thereof |
| CN105238389A (en) * | 2015-10-12 | 2016-01-13 | 中节能万润股份有限公司 | Novel organic electroluminescent material and use thereof |
Cited By (2)
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|---|---|---|---|---|
| CN109574858A (en) * | 2017-09-28 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of spiral shell dimethylanthracene fluorenes class organic compound and its application on organic electroluminescence device |
| CN109574858B (en) * | 2017-09-28 | 2021-04-30 | 中节能万润股份有限公司 | Spiro-dimethyl anthracene fluorene organic compound and application thereof in organic electroluminescent device |
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Denomination of invention: Fluorene spirodibenzoacridine organic electroluminescent material and its application Effective date of registration: 20211202 Granted publication date: 20190723 Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd. Pledgor: VALIANT Co.,Ltd. Registration number: Y2021980013807 |
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| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20220823 Granted publication date: 20190723 Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd. Pledgor: VALIANT Co.,Ltd. Registration number: Y2021980013807 |