CN102977006A - Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof - Google Patents
Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof Download PDFInfo
- Publication number
- CN102977006A CN102977006A CN2012105607149A CN201210560714A CN102977006A CN 102977006 A CN102977006 A CN 102977006A CN 2012105607149 A CN2012105607149 A CN 2012105607149A CN 201210560714 A CN201210560714 A CN 201210560714A CN 102977006 A CN102977006 A CN 102977006A
- Authority
- CN
- China
- Prior art keywords
- pyridine
- fluorene
- add
- organic
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 57
- YMTQRYMSWUKLIN-UHFFFAOYSA-N C1=CC=NC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 Chemical compound C1=CC=NC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 YMTQRYMSWUKLIN-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 238000002347 injection Methods 0.000 claims abstract description 3
- 239000007924 injection Substances 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 238000001035 drying Methods 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 16
- YDXRPPDCHGHWMY-UHFFFAOYSA-N 9-pyridin-2-ylfluoren-9-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(O)C1=CC=CC=N1 YDXRPPDCHGHWMY-UHFFFAOYSA-N 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 10
- 238000004440 column chromatography Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 8
- 239000012265 solid product Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 claims description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 claims description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 241000143437 Aciculosporium take Species 0.000 claims 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002274 desiccant Substances 0.000 claims 1
- 239000003599 detergent Substances 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 238000013461 design Methods 0.000 abstract description 6
- 238000005516 engineering process Methods 0.000 abstract description 6
- 238000010791 quenching Methods 0.000 abstract description 4
- 230000000171 quenching effect Effects 0.000 abstract description 4
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- 239000000539 dimer Substances 0.000 abstract 1
- 239000012769 display material Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000009477 glass transition Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 32
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 12
- 150000002220 fluorenes Chemical class 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 238000000605 extraction Methods 0.000 description 8
- 230000004044 response Effects 0.000 description 8
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 6
- 238000007306 functionalization reaction Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- -1 aryl fluorene Chemical compound 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000003335 steric effect Effects 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- CVSBRGRSQUGIKO-UHFFFAOYSA-N 9-(2-chloroethyl)carbazole Chemical compound C1=CC=C2N(CCCl)C3=CC=CC=C3C2=C1 CVSBRGRSQUGIKO-UHFFFAOYSA-N 0.000 description 1
- JDINBEDUGBFLEC-UHFFFAOYSA-N 9-pyridin-2-ylcarbazole Chemical compound N1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 JDINBEDUGBFLEC-UHFFFAOYSA-N 0.000 description 1
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000840 electrochemical analysis Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000004832 voltammetry Methods 0.000 description 1
Images
Landscapes
- Pyridine Compounds (AREA)
Abstract
吡啶芴类有机电致磷光主体发光材料及其制备方法涉及新一代有机发光显示材料与技术，因其刚性结构而具有高的三线态能级及良好的空穴注入和传输性能，三维大体积空间位阻效应使其具有稳定的无定形态，而广泛用于有机发光二极管。本发明为一种吡啶芴类的主体材料，具体设计结构如下：
Pyridine fluorene-based organic electrophosphorescent host light-emitting materials and their preparation methods relate to a new generation of organic light-emitting display materials and technologies, which have high triplet energy levels and good hole injection and transport properties due to their rigid structures, and three-dimensional large-volume space The steric hindrance effect makes it have a stable amorphous form, and it is widely used in organic light-emitting diodes. The present invention is a main body material of pyridine fluorene, and the specific design structure is as follows:
Description
Technical field
The present invention is specifically related to make the preparation method of its functionalization based on 9 hydroxyls with 9-hydroxyl-9-(2-pyridyl) fluorenes with the aromatic ring replacement, and relates to step and raw material that these materials adopt in preparation process.
Background technology
Since Deng Qingyun in 1987 had reported that the high brightness low voltage has the Organic Light Emitting Diode of sandwich structure, organic electroluminescent LED was as flat pannel display of future generation and solid state lighting technology and be subject to numerous scientific workers' great attention and greatly research enthusiasm of industry member elite.Indicating meter with inorganic materials is compared, organic elctroluminescent device has its many advantages that can't reach, as: material source is wide, energy consumption is little, lightweight, volume is little, manufacturing process is simple, contrast gradient is high, the visual angle is wide, driving voltage is low, color is adjustable, fast response time, luminous efficiency high, flexible show etc.Therefore, being described as " 21 century flat panel display ", is the technique of display of generally acknowledge the most desirable of industry and tool development prospect.。
Electroluminescent organic material is divided into fluorescence and phosphorescence two class materials.And organic electroluminescent fluorescent materials makes its device internal quantum efficiency have 25% theoretical limit because its triplet excitons exists spin to prohibit and can not effectively utilize its triplet excitons energy always.In contrast, the organic molecule electromechanical phosphorescent material since because of the Spin-orbit coupling interaction of heavy metal so that its triplet excitons is effectively luminous by passing through between being, thereby so that the organic molecule phosphor material break through the one theory of internal quantum efficiency 25% and reach 100%.The performance such as in addition, its simple preparation method and color be adjustable also enjoys scientific worker's favor.Baldo in 2001 etc. are (ppy)
2Ir (acac) is entrained among the TAZ, has prepared the high efficiency phosphorescent device, and the internal quantum efficiency of this device almost reaches 100 %, and its external quantum efficiency reaches 19%.So that the efficient of electroluminescent device obtains unprecedented raising and has caused great sensation.Yet organic electro phosphorescent device normally is doped to guest materials in the material of main part, to prevent that guest materials under solid state concentration quenching occuring or triplet state is buried in oblivion.Therefore preparing effective material of main part is the key of preparation stability and high efficiency phosphorescence device.In order to obtain efficient phosphorescence device, desirable material of main part need to satisfy following condition: at first, material of main part need to have suitable triplet (triplet that is material of main part is greater than guest materials), to prevent the energy counter-rotating; Secondly, suitable HOMO and lumo energy can be complementary with the energy level of adjacent carrier blocking layers, reduce driving voltage and improve luminous efficiency; Again, material of main part will have high thermostability and good film forming characteristics, to improve the stability of device; At last, material of main part need to have good carrier injection and transmittability and effectively equilbrium carrier make its effective recombination luminescence in guest materials, to improve the luminous efficiency of device.Therefore, the synthetic effective material of main part of design is the key of preparation stability and high efficiency luminescent device.
Pyridine fluorenes class has stable amorphous state and high thermostability because having larger three-dimensional space steric effect, can concentration quenching and the triplet state of establishment object phosphor material under filminess bury in oblivion.In addition, fluorenes has higher triplet (2.95 eV), can make it both have good photoelectric properties by its 9-position is modified and have suitable triplet because of non-conjugated connection.Based on this thought, the present invention passes through friedel-crafts reaction with 9-hydroxyl-9 (2-pyridyl) fluorenes, succinctly prepared efficiently a series of luminescent materials with 9-hydroxyl-9 (2-pyridyl) fluorenes functionalization, and to having carried out preliminary study in the application aspect the OLEDs.
In a word, the present invention is under the prerequisite to current electroluminescent organic material overall understanding, and tracking organic electronic devices forward position is dynamic, launches around preparation and the dependent interaction mechanism thereof synthetic, El element of electroluminescent organic material.Take molecular designing as guidance, the effective material of main part of design synthesizing stable, the phosphorescence device of preparation stability and high efficiency.
Summary of the invention
Technical problem:Purpose of the present invention provides a kind of pyridine fluorenes class luminescent material and its preparation method and application, and design is synthetic based on a kind of pyridine fluorenes class luminescent material, and effective material of main part is stablized in preparation, and there is widespread use in it aspect electroluminescent, the memory device.
Technical scheme:The present invention is a kind of pyridine fluorenes class luminescent material and its preparation method and application, and this material is 9 hydrogen atom positions of fluorenes in the pyridine fluorenes class to be replaced with different aromatic rings make its functionalization, and it has following structure:
General formula
I
General formula
IIn, n=1 or 2, Ar are aromatic ring structure, its array structure specific as follows:
。
General formula
IThe compound of representative all contains pyridine fluorenes class, and the functional functional group A r of all introducings all is connected to 9 of fluorenes.
The preparation method of pyridine fluorenes organic electrofluorescent main body luminescent material of the present invention is:
A. get the 2-bromopyridine and join single necked round bottom flask, low temperature stirs under dry ice acetone and nitrogen protection, getting n-Butyl Lithium slowly adds in the reactor, low-temp reaction 0.5-5 hour, get Fluorenone and inject constant pressure funnel with the THF dissolving, and add the ether dilution, be added drop-wise in the reactor, low-temp reaction 1-5 hour, normal-temperature reaction then; Use water treatment, transfer pH to be about neutrality with acetic acid, use dichloromethane extraction, the organic phase anhydrous magnesium sulfate drying, concentrated, column chromatography gets product;
B. get in 9-hydroxyl-9-(2-pyridyl) fluorenes, 2-thiotolene, the acetic acid heated and stirred dissolving adding reactor, then add the vitriol oil, be heated to back flow reaction 10-48 hour, question response is cooled to room temperature, adding cold water stirs, then add aqueous sodium hydroxide solution to solution and be alkalescence, with dichloromethane extraction repeatedly, merge the organic phase anhydrous magnesium sulfate drying; After the drying, decompress filter is also used the washed with dichloromethane siccative, gained filtrate is removed most of solvent with the Rotary Evaporators concentrating under reduced pressure, the crude product that obtains concentrating; Then column chromatography, take ethyl acetate and sherwood oil as washing composition, after the purification white solid product.
Spiro-iridium organic electrophosphorescenmaterial material of the present invention is used for organic electroluminescent diode apparatus, wherein the structure of LED device is transparent anode/luminescent layer/electron injecting layer/negative electrode, wherein, luminescent layer is the Subjective and Objective system, and spiral shell fluorenes xanthene title complex is as the guest materials of luminescent layer.
Device architecture is as follows: suitable guest materials is doped to preparation red, green, blue three primary colours organic electroluminescence device in the synthetic pyridine fluorenes class of design.
But the present invention has 3-D solid structure establishment concentration quenching in conjunction with the pyridine fluorenes, introduces different functional luminous energy group's timely adjustment spectrum and energy level thereof for 9 that are combined in simultaneously fluorenes, thereby reaches synthetic succinct efficiently material of main part.
Beneficial effect:Characterized the complex whorl aryl fluorene material structure by ultimate analysis, infrared spectra (FTIR), nucleus magnetic resonance (NMR), chromaticness online (GCMS), gel chromatography (GPC), by the thermostability that thermogravimetric analysis and differential thermal analysis have been tested material, characterized their light, electrochemical properties by Ultraluminescence spectrum and cyclic voltammetric method.This class material shows good thermostability in thermogravimetric analysis and differential thermal analysis, ultraviolet, fluorescence and electrochemical analysis show that it has good photoelectric properties.Therefore, this class material can be widely used in Organic Light Emitting Diode, organic laser, Organic Electricity memory device, organic field-effect tube etc.
On this basis, design preliminary electroluminescent device and estimated pyridine fluorenes luminescent properties.Wherein the structure of device is transparent anode/luminescent layer/electron injecting layer/negative electrode, wherein the pyridine fluorenes by the vacuum evaporation mode prepare, negative electrode prepares by vacuum coating technology.Experimental result shows: these pyridine fluorenes have shown efficient phosphorescent emissions performance, with FIrpic, Ir (ppy)
3, Ir (MDQ)
2(acac) etc. guest materials is by steamings degree technology realization red, green, blue three-color light-emitting technology.
Major advantage of the present invention is:
1. simple, the mild condition of synthesis step;
2. high thermal stability and second-order transition temperature have been kept.
3. has suitable triplet
4. have suitable HOMO and lumo energy
5. has large space steric effect
Description of drawings
Fig. 1. 9-(2-pyridyl)-9-(2-thienyl) fluorenes
1HNMR figure;
Fig. 2. 9-(2-pyridyl)-9-(2-thiotolene base) fluorenes
1HNMR figure;
Fig. 3. 9-(2-pyridyl)-9-(2-(2,2-bithienyl)) fluorenes
1HNMR figure;
Fig. 4. 2,2-two (9-(2-pyridine)-fluorenyl)-2,2 ', 2 ' '-three thiophene
1HNMR figure;
Fig. 5. 9-(2-chloroethyl)-3,6-two (9-(2-pyridine)-fluorenyl) carbazole
1HNMR figure;
Fig. 6. 3,6-two (9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole and
1HNMR figure;
Fig. 7. 3-(9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole
1HNMR figure;
Fig. 8. with 3-(9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole electroluminescent spectrogram.
Fig. 9. 3,6-two (9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole electroluminescent spectrogram.
Figure 10 2, and 2-two (9-(2-pyridine)-fluorenyl)-2,2 ', 2 ' '-three thiophene is respectively the main body material of device
Material electroluminescent spectrogram.
The brightness of Figure 11 blue-light device B1-B4-voltage-to-current densimetric curve.
The external quantum efficiency of Figure 12 blue-light device B1-B4-current density curve.
Figure 13 is the structural representation of luminescent device.
Embodiment
Further describe technical scheme of the present invention below in conjunction with embodiment, but these embodiment and unrestricted embodiments of the present invention.The present invention has multiple different embodiment, has more than to be limited to content described in this specification sheets.Those skilled in the art is in the situation of the present application spirit, and the scheme of finishing should be within the scope of the invention.
Embodiment 1:9-(2-pyridyl)-9-(2-thienyl) fluorenes
Get successively 9-hydroxyl-9 (2-pyridyl) fluorenes (0.5180 g, 2 mmol), thiophene (1.28 mL, 16 mmol), the dissolving of acetic acid 200 mL heated and stirred, then add the vitriol oil 4 mL and be heated to 120 ℃ of 24 h that reflux.Question response is cooled to room temperature, adds about 100 mL cold water and stirs, and then adds aqueous sodium hydroxide solution to solution and is alkalescence, with dichloromethane extraction repeatedly, merges the organic phase anhydrous magnesium sulfate drying.After the drying, decompress filter is also used the washed with dichloromethane siccative, gained filtrate is removed most of solvent with the Rotary Evaporators concentrating under reduced pressure, the crude product that obtains concentrating.Then column chromatography, take ethyl acetate and sherwood oil as washing composition, after the purification white solid product (productive rate: 40%).GC-MS?(EI)?m/z?325?[M
+];1H?NMR?(400?MHz,?CDCl
3):?δ?(ppm)?8.66?(s,?1H),?7.78?(D,?
J?=?7.52,?2H),?7.69?(D,?
J?=?7.57,?2H),?7.46?(m,?1H),?7.40?(t,?
J?=?6.54,?2H),?7.31?(t,?
J?=?6.57,?2H),?7.13?(m,?2H),?7.05?(D,?
J?=?7.96,?1H),?6.86?(t,?
J?=?3.66,?1H),?6.77?(D,?
J?=?4.62,?1H)。
Synthesizing of embodiment 2:9-(2-pyridyl)-9-(2-thiotolene base) fluorenes:
Get successively 9-hydroxyl-9 (2-pyridyl) fluorenes (0.5180 g, 2 mmol), 2-thiotolene (1.57 mL, 16 mmol), the dissolving of acetic acid 200 mL heated and stirred, then add the vitriol oil 4 mL and be heated to 120 ℃ of backflow 24h.Question response is cooled to room temperature, adds about 100 mL cold water and stirs, and then adds aqueous sodium hydroxide solution to solution and is alkalescence, with dichloromethane extraction repeatedly, merges the organic phase anhydrous magnesium sulfate drying.After the drying, decompress filter is also used the washed with dichloromethane siccative, gained filtrate is removed most of solvent with the Rotary Evaporators concentrating under reduced pressure, the crude product that obtains concentrating.Then column chromatography, take ethyl acetate and sherwood oil as washing composition, after the purification white solid product (productive rate: 42%).GC-MS?(EI)?m/z?325?[M
+];1H?NMR?(400?MHz,?CDCl
3):?δ?(ppm)?8.70?(s,?1H),?7.77?(D,?
J?=?7.55,?2H),?7.68?(D,?
J?=?7.53,?2H),?7.50?(m,?1H),?7.39?(t,?
J?=?7.28,?2H),?7.31?(t,?
J?=?7.44,?2H),?7.11?(t,?
J?=?4.83,?1H),?7.05?(D,?
J?=?7.99,?1H),?6.52?(m,?2H),?2.38?(s,?3H)。
Synthesizing of embodiment 3:9-(2-pyridyl)-9-(2-(2,2-bithienyl)) fluorenes:
Get successively 9-hydroxyl-9 (2-pyridyl) fluorenes (0.5180 g, 2 mmol), 2, then 2-two bithiophenes (0.1663 g, 1 mmol), the dissolving of acetic acid 200 mL heated and stirred add the vitriol oil 4 mL and are heated to 120 ℃ of backflow 24h.Question response is cooled to room temperature, adds about 100 mL cold water and stirs, and then adds aqueous sodium hydroxide solution to solution and is alkalescence, with dichloromethane extraction repeatedly, merges the organic phase anhydrous magnesium sulfate drying.After the drying, decompress filter is also used the washed with dichloromethane siccative, gained filtrate is removed most of solvent with the Rotary Evaporators concentrating under reduced pressure, the crude product that obtains concentrating.Then column chromatography, take ethyl acetate and sherwood oil as washing composition, after the purification white solid product (productive rate: 30%).GC-MS?(EI)?m/z?325?[M
+];1H?NMR?(400?MHz,?CDCl
3):?δ?(ppm)?8.70?(s,?1H),?7.80?(d,?
J?=?7.35,?2H),?7.73?(d,?
J?=?7.57,?2H),?7.45?(m,?3H),?7.40?(t,?
J?=?7.43,?2H),?7.15?(m,?2H),?7.0613?(m,?2H),?6.93?(m,?2H),?6.67?(m,?1H)。
Embodiment 4:2,2-two (9-(2-pyridine)-fluorenyl)-2,2 ', 2 ' '-three thiophene synthetic:
Get successively 9-hydroxyl-9 (2-pyridyl) fluorenes (0.7800 g, 3 mmol), 2,2 ', 2 ' '-dissolving of terthienyl (0.7400 g, 3 mmol), acetic acid 200 mL heated and stirred, then add the vitriol oil 4 mL and be heated to 120 ℃ of backflow 24h.Question response is cooled to room temperature, adds about 100 mL cold water and stirs, and then adds aqueous sodium hydroxide solution to solution and is alkalescence, with dichloromethane extraction repeatedly, merges the organic phase anhydrous magnesium sulfate drying.After the drying, decompress filter is also used the washed with dichloromethane siccative, gained filtrate is removed most of solvent with the Rotary Evaporators concentrating under reduced pressure, the crude product that obtains concentrating.Then column chromatography, take ethyl acetate and sherwood oil as washing composition, after the purification white solid product (productive rate, 17.1 %).GC-MS?(EI)?m/z?325?[M
+];1H?NMR?(400?MHz,?CDCl
3):?δ?(ppm)?8.70?(s,?1H),?8.60?(s,?1H),?7.99?(d,?
J?=?7.86,?2H),?7.70?(d,?
J?=?7.63,2H),?7.61?(d,?
J?=?7.36,?2H),?7.53?(d,?
J?=?7.16,?2H),?7.45?(m,?3H),?7.33?(m,?3H),?7.28?(d,?
J?=7.39,?1H),?7.17?(m,?5H),?7.04?(m,?2H),?6.89?(d,?
J?=?7.19,?1H),?6.71?(d,?
J?=?3.61,?1H),?6.66?(d,?
J?=?5.44,?1H),?6.62?(d,?
J?=?3.70,?1H),?6.43?(d,?
J?=?3.70,?1H),?5.84?(d,?
J?=?3.77,?1H)。
Embodiment 5:9-(2-chloroethyl)-3,6-two (9-(2-pyridine)-fluorenyl) carbazole synthetic
Get successively 9-(2-chloroethyl) carbazole (0.4600 g, 2 mmol), 9-hydroxyl-9 (2-pyridyl) fluorenes (1.0400 g, 4 mmol), acetic acid 200 mL heated and stirred dissolvings, then add the vitriol oil 4 mL and be heated to 120 ℃ of backflow 24h.Question response is cooled to room temperature, adds about 100 mL cold water and stirs, and then adds aqueous sodium hydroxide solution to solution and is alkalescence, with dichloromethane extraction repeatedly, merges the organic phase anhydrous magnesium sulfate drying.After the drying, decompress filter is also used the washed with dichloromethane siccative, gained filtrate is removed most of solvent with the Rotary Evaporators concentrating under reduced pressure, the crude product that obtains concentrating.Then column chromatography, take ethyl acetate and sherwood oil as washing composition, after the purification white solid product (productive rate: 16 %).GC-MS?(EI)?m/z?325?[M
+];1H?NMR?(400?MHz,?CDCl
3):?δ?(ppm)?8.62?(s,?2H),?7.78?(d,?
J?=?7.52,?2H),?7.62?(t,?
J?=?7.28,?2H),?7.47?(t,?
J?=?7.77,2H),?7.37?(t,?
J?=?7.23,?2H),?7.28?(s,?1H),?7.24?(s,?1H),?7.10?(m,?10H),?4.45?(t,?
J?=7.14,?2H),?3.71?(t,?
J?=7.15,?2H)。
Embodiment 6:3,6-two (9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole and 3-(9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole synthetic
Get successively N-(2-pyridyl) carbazole (1.4600 g, 6 mmol), 9-hydroxyl-9-(2-pyridyl) fluorenes (1.5500 g, 6 mmol), acetic acid 200 mL heated and stirred dissolvings, then add the vitriol oil 4 mL and be heated to 120 ℃ of 24 h that reflux.Question response is cooled to room temperature, adds about 100 mL cold water and stirs, and then adds aqueous sodium hydroxide solution to solution and is alkalescence, with dichloromethane extraction repeatedly, merges the organic phase anhydrous magnesium sulfate drying.After the drying, decompress filter is also used the washed with dichloromethane siccative, gained filtrate is removed most of solvent with the Rotary Evaporators concentrating under reduced pressure, the crude product that obtains concentrating.Then column chromatography, take ethyl acetate and sherwood oil as washing composition, after the purification white solid product (productive rate, 3,6-two (9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole: 43.8%; 3-(9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole: 4.6 %).
3,6-two (9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole: MODI-TOF (EI) m/z 726 [M
+];
1H NMR (400 MHz, CDCl
3):
δ(ppm) 8.74 (s, 3H), 8.13 (d,
J=7.84,5H), 7.93 (t,
J=7.88,3H), 7.85 (d,
J=8.25,5H), 7.65 (d,
J=8.18,3H), 7.45 (t,
J=7.87,6H), 7.32 (m, 9H).
13C NMR (100 MHz, CDCl
3):
δ(ppm) 151.87,149.66,139.58,138.45,126.21,124.31,121.22,120.91,120.21,119.09,111.12.
3-(9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole: GC-MS (EI) m/z 485 [M
+];
1H NMR (400 MHz, CDCl
3):
δ(ppm) 8.67 (s, 2H), 7.87 (m, 2H), 7.81 (t,
J=7.89,3H), 7.71 (m, 4H), 7.58 (d,
J=8.18,1H), 7.50 (t,
J=7.80,1H), 7.38 (m, 3H), 7.30 (t,
J=7.50,2H), 7.23 (m, 2H), 7.18 (t,
J=2.45,1H), 7.14 (m, 2H).
13C NMR (100 MHz, CDCl
3):
δ(ppm) 162.35,151.90,149.78,140.45,139.77,138.71,138.33,127.72,127.67,126.91,126.74,126.04,124.38,124.45,121.66,121.54,120.98,120.66,120.25,120.16,119.03,118.77,111.08,67.28.
Fig. 8 is to be with 3 with 3-(9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole, Fig. 9,6-two (9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole, Figure 10 are with 2,2-two (9-(2-pyridine)-fluorenyl)-2,2 ', 2 ' '-three thiophene is respectively blue, green, the red three kinds of color electroluminescent spectrograms of material of main part of device; Wherein
B1,
B4,
G1,
R1All take 3-(9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole as material of main part;
B2,
G2,
R2Be material of main part with 3,6-two (9-(2-pyridine)-fluorenyl)-N-(2-pyridyl) carbazole all;
B3,
G3,
R3All be divided into material of main part with 2,2-two (9-(2-pyridine)-fluorenyl)-2,2 ', 2 ' '-three thiophene.Respectively with Firpic, Ir (ppy)
3, Ir (MDQ)
2(acac) blue, green, the red three primary colours electroluminescent device of guest materials preparation.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012105607149A CN102977006A (en) | 2012-12-21 | 2012-12-21 | Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012105607149A CN102977006A (en) | 2012-12-21 | 2012-12-21 | Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102977006A true CN102977006A (en) | 2013-03-20 |
Family
ID=47851407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012105607149A Pending CN102977006A (en) | 2012-12-21 | 2012-12-21 | Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102977006A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103951813A (en) * | 2014-03-31 | 2014-07-30 | 南京邮电大学 | 9-Aryl substituted flourenyl conjugated polyelectrolyte, and preparation method and application thereof |
| WO2015084021A1 (en) * | 2013-12-04 | 2015-06-11 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR20150108332A (en) * | 2014-03-17 | 2015-09-25 | 롬엔드하스전자재료코리아유한회사 | Electron Buffering Material and Organic Electroluminescent Device |
| JP2015189694A (en) * | 2014-03-27 | 2015-11-02 | 旭有機材工業株式会社 | Fluorene derivative, production method thereof, compound, composition and hardened product |
| WO2015167199A1 (en) * | 2014-04-29 | 2015-11-05 | Rohm And Haas Electronic Materials Korea Ltd. | Electron transport material and organic electroluminescent device comprising the same |
| KR20150124886A (en) * | 2014-04-29 | 2015-11-06 | 롬엔드하스전자재료코리아유한회사 | Electron transport material and an organic electroluminescence device comprising the same |
| CN105199712A (en) * | 2015-09-24 | 2015-12-30 | 信阳师范学院 | Triphenylamine/fluorine sterically hindered bipolar luminescent material and preparing method and application thereof |
| WO2018041123A1 (en) * | 2016-08-31 | 2018-03-08 | 江苏三月光电科技有限公司 | Compound with nucleus of fluorene and six-membered nitrogen-containing heterocycle and application thereof in organic light emitting device |
| WO2018117562A1 (en) * | 2016-12-20 | 2018-06-28 | 주식회사 두산 | Organic compound and organic electroluminescent device using same |
| WO2018117561A1 (en) * | 2016-12-23 | 2018-06-28 | 주식회사 두산 | Organic compound and organic electroluminescent device using same |
| KR20180097806A (en) * | 2017-02-23 | 2018-09-03 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| CN109575012A (en) * | 2017-09-28 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of organic compound and its application containing fluorenes and pyridine diindyl |
| CN111499557A (en) * | 2020-04-23 | 2020-08-07 | 深圳大学 | An organic host material and electroluminescent device |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006131783A (en) * | 2004-11-08 | 2006-05-25 | Konica Minolta Holdings Inc | Material for organic electroluminescent element, organic electroluminescent element, lighting apparatus and display |
| WO2012078770A2 (en) * | 2010-12-08 | 2012-06-14 | Georgia Tech Research Corporation | Bis(sulfonyl)biaryl derivatives as electron transporting and/or host materials |
| JP2012211089A (en) * | 2011-03-30 | 2012-11-01 | Sumitomo Chemical Co Ltd | Method for producing fluorene-based compound |
-
2012
- 2012-12-21 CN CN2012105607149A patent/CN102977006A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006131783A (en) * | 2004-11-08 | 2006-05-25 | Konica Minolta Holdings Inc | Material for organic electroluminescent element, organic electroluminescent element, lighting apparatus and display |
| WO2012078770A2 (en) * | 2010-12-08 | 2012-06-14 | Georgia Tech Research Corporation | Bis(sulfonyl)biaryl derivatives as electron transporting and/or host materials |
| JP2012211089A (en) * | 2011-03-30 | 2012-11-01 | Sumitomo Chemical Co Ltd | Method for producing fluorene-based compound |
Non-Patent Citations (2)
| Title |
|---|
| KEN-TSUNG WONG，等: "Nonconjugated Hybrid of Carbazole and Fluorene: A Novel Host Material for Highly Efficient Green and Red Phosphorescent OLEDs", 《ORGANIC LETTERS》, vol. 7, no. 24, 28 October 2005 (2005-10-28), pages 5361 - 5364 * |
| PING-I SHIH，等: "Novel Carbazole/Fluorene Hybrids: Host Materials for Blue Phosphorescent OLEDs", 《ORGANIC LETTERS》, vol. 8, no. 13, 27 May 2006 (2006-05-27), pages 2799 - 2802 * |
Cited By (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105745200A (en) * | 2013-12-04 | 2016-07-06 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| WO2015084021A1 (en) * | 2013-12-04 | 2015-06-11 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR20150064878A (en) * | 2013-12-04 | 2015-06-12 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR102184893B1 (en) * | 2013-12-04 | 2020-12-01 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN105745200B (en) * | 2013-12-04 | 2021-08-17 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent devices comprising the same |
| JP2017501127A (en) * | 2013-12-04 | 2017-01-12 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Novel organic electroluminescent compound and organic electroluminescent device including the same |
| KR20150108332A (en) * | 2014-03-17 | 2015-09-25 | 롬엔드하스전자재료코리아유한회사 | Electron Buffering Material and Organic Electroluminescent Device |
| KR102411748B1 (en) * | 2014-03-17 | 2022-06-23 | 롬엔드하스전자재료코리아유한회사 | Electron Buffering Material and Organic Electroluminescent Device |
| JP2015189694A (en) * | 2014-03-27 | 2015-11-02 | 旭有機材工業株式会社 | Fluorene derivative, production method thereof, compound, composition and hardened product |
| CN103951813A (en) * | 2014-03-31 | 2014-07-30 | 南京邮电大学 | 9-Aryl substituted flourenyl conjugated polyelectrolyte, and preparation method and application thereof |
| CN106232591A (en) * | 2014-04-29 | 2016-12-14 | 罗门哈斯电子材料韩国有限公司 | Electron transport material and the Organnic electroluminescent device comprising it |
| JP2017515304A (en) * | 2014-04-29 | 2017-06-08 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Electron transport material and organic electroluminescent device including the same |
| EP3137451A4 (en) * | 2014-04-29 | 2018-01-03 | Rohm And Haas Electronic Materials Korea Ltd. | Electron transport material and organic electroluminescent device comprising the same |
| KR102427918B1 (en) * | 2014-04-29 | 2022-08-03 | 롬엔드하스전자재료코리아유한회사 | Electron transport material and an organic electroluminescence device comprising the same |
| KR20150124886A (en) * | 2014-04-29 | 2015-11-06 | 롬엔드하스전자재료코리아유한회사 | Electron transport material and an organic electroluminescence device comprising the same |
| WO2015167199A1 (en) * | 2014-04-29 | 2015-11-05 | Rohm And Haas Electronic Materials Korea Ltd. | Electron transport material and organic electroluminescent device comprising the same |
| CN106232591B (en) * | 2014-04-29 | 2020-08-11 | 罗门哈斯电子材料韩国有限公司 | Electron transport material and organic electroluminescent device comprising the same |
| US10818846B2 (en) | 2014-04-29 | 2020-10-27 | Rohm And Haas Electronic Materials Korea Ltd. | Electron transport material and organic electroluminescent device comprising the same |
| CN105199712A (en) * | 2015-09-24 | 2015-12-30 | 信阳师范学院 | Triphenylamine/fluorine sterically hindered bipolar luminescent material and preparing method and application thereof |
| WO2018041123A1 (en) * | 2016-08-31 | 2018-03-08 | 江苏三月光电科技有限公司 | Compound with nucleus of fluorene and six-membered nitrogen-containing heterocycle and application thereof in organic light emitting device |
| KR102024421B1 (en) | 2016-12-20 | 2019-09-23 | 주식회사 두산 | Organic compound and organic electroluminescent device using the same |
| KR20180071892A (en) * | 2016-12-20 | 2018-06-28 | 주식회사 두산 | Organic compound and organic electroluminescent device using the same |
| WO2018117562A1 (en) * | 2016-12-20 | 2018-06-28 | 주식회사 두산 | Organic compound and organic electroluminescent device using same |
| WO2018117561A1 (en) * | 2016-12-23 | 2018-06-28 | 주식회사 두산 | Organic compound and organic electroluminescent device using same |
| KR20180097806A (en) * | 2017-02-23 | 2018-09-03 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| KR102834564B1 (en) | 2017-02-23 | 2025-07-15 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| CN109575012A (en) * | 2017-09-28 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of organic compound and its application containing fluorenes and pyridine diindyl |
| CN111499557A (en) * | 2020-04-23 | 2020-08-07 | 深圳大学 | An organic host material and electroluminescent device |
| CN111499557B (en) * | 2020-04-23 | 2022-05-31 | 深圳大学 | An organic host material and electroluminescent device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102977006A (en) | Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof | |
| CN102786508A (en) | Spiro-fluorene-9,9-xanthene bipolar luminescent material, its preparation method and its application method | |
| CN103664894B (en) | A kind of 6H naphtho-[2,1,8,7 klmn] a word used for translation derivant and application thereof | |
| CN109678844B (en) | Orange red photo-thermal activation delayed fluorescence material and organic electroluminescent device | |
| CN110003260A (en) | Boron heterocyclic compound, display panel, and display device | |
| CN105440004B (en) | A kind of electroluminescent organic material and its application | |
| CN102911145A (en) | Dibenzo-heterocyclic spirobifluorene compound, preparation method thereof and organic electrophosphorescent device | |
| CN104370904B (en) | A kind of electron transport material, preparation method and application thereof | |
| CN110437211A (en) | A kind of thermal activation delayed fluorescence material and its preparation method and application | |
| CN102653546B (en) | Bipolarity Blue-light emitting host material and preparation method thereof and organic electroluminescence device | |
| CN109503427B (en) | A D-A type organic blue fluorescent material and its preparation method and application | |
| CN103539737B (en) | A kind of azepine phenanthro- fluorene kind derivative, preparation method and electroluminescent fluorescent luminescent device | |
| CN106941133B (en) | A kind of organic light-emitting device and preparation method thereof | |
| CN110218212B (en) | Nitrogen heterocyclic compound, display panel and display device | |
| CN112358480A (en) | Compound based on imidazo-cyclopent-isoquinoline as receptor and application thereof | |
| CN102827203A (en) | A kind of phosphorescence host material and its preparation method and application | |
| CN108017648A (en) | A kind of perimidine derivative and its application | |
| CN102653677B (en) | Bipolar blue-light main material and preparation method thereof and organic electroluminescent device | |
| CN103666460A (en) | Low-triplet-state-energy-level blue-light phosphorescent main body material and application thereof | |
| CN107382994A (en) | Oxadiazole loop coil aromatic hydrocarbons steric hindrance type bipolarity luminescent material of 2,5 diphenyl 1,3,4 and preparation method thereof | |
| CN116375708B (en) | Organic electroluminescent material based on indolospiroacridine and application of organic electroluminescent material in OLED | |
| CN103172652A (en) | Tetraphenyl silicon containing organic semiconductor material and preparation method thereof and organic electroluminescent device | |
| CN115028626B (en) | Thermally-induced delayed fluorescent material and preparation method and application thereof | |
| CN116554200B (en) | Nitrogen-containing organic compound, application thereof and organic electroluminescent device | |
| CN105131940A (en) | Organic luminescent material containing spirobifluorene and dibenzothiophene and luminescent device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20130320 |