CN102503937B - Bipolar organic material containing pyridine and carbazole and preparation method and application thereof - Google Patents
Bipolar organic material containing pyridine and carbazole and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a bipolar organic material containing pyridine and carbazole and a preparation method and an application thereof. In the material, pyridine is taken as a core; carbazole is introduced to the periphery of the pyridine; the pyridine core and the carbazole periphery are connected through hexahydric nitrogen heterocyclic rings such as phenyl or pyridine, pyrimidine, pyrazine and the like; and by adjusting the quantity of the hexahydric nitrogen heterocyclic rings and the positions of nitrogen atoms, the aims of adjusting and controlling the molecular orbit energy level, the singlet energy level and the triplet energy level of the material are fulfilled. The material serving as a main material of a phosphorescent material can be applied to the luminous layer of an organic light emitting diode.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, be specifically related to a kind of bipolar organic material that contains pyridine and carbazole and preparation method thereof with application in organic electroluminescent LED.
Background technology
Recent two decades comes, and organic electroluminescent LED (OLED), because having efficient, low voltage drive, is easy to the advantages such as big area preparation and panchromatic demonstration and has broad application prospects, and obtains people's extensive concern.This research starts from eighties of last century fifties, adopts sandwich device architecture until doctor Deng Qingyun of Kodak in 1987 waits in patent US4356429, and the OLED device of developing luminosity under 10V direct voltage drive reaches 1000cd/m
2, make OLED obtain epoch-making development.
Organic electroluminescent is mainly divided into fluorescence and phosphorescence, but according to spin quantum statistical theory, the probability of singlet state exciton and triplet exciton is 1: 3, is 25% from the theoretical limit of the fluorescence of singlet state exciton radiative transition, and the theoretical limit of the fluorescence of triplet exciton radiative transition is 75%.How to utilize the energy of 75% triplet excitons to become the task of top priority.The discovery electrophosphorescence phenomenons such as Forrest in 1997 have broken through the restriction of electroluminescent organic material quantum yield 25% efficiency.Within 1999, Forrest is by green glow dopant material Ir (ppy)
3be entrained in material of main part 4,4 '-N with 6% quality doping content, in N '-bis-carbazyl-biphenyl (CBP), obtain external quantum efficiency 8%, efficiency, up to 31 lm/W, is much higher than fluorescent material device, causes the extensive concern of people to metal complexes phosphor material.From then on, people carry out a large amount of research to phosphor material.
And the use of phosphor material, for inhibition concentration delustring need be doped to phosphor material in the material of main part with charge-transporting, therefore require material of main part to there is the triplet higher than phosphor material, to promote material of main part to shift to the energy of phosphor material, effectively prevent from being shifted to the reverse energy of material of main part by phosphor material simultaneously.In addition, the combination again in luminescent layer because of electronics and hole, this just requires material of main part to have hole and electron-transporting simultaneously.Normally used material of main part, as CBP, because being mainly made up of the carbazole unit of electron donor(ED), its hole transport ability is higher than electron-transporting, thereby easily causes the imbalance in hole and electronics in luminescent layer and finally cause the low of device efficiency.Therefore, be badly in need of the material of main part that exploitation has hole and electron-transporting simultaneously, namely usually said bipolar materials, in promoting that electronics and hole are injected and transmitted to luminescent layer, effectively improve the balance in hole and electronics in luminescent layer, thereby reach the object that improves device efficiency.
Summary of the invention
In order to overcome prior art above shortcomings, one of object of the present invention is to provide the bipolar organic material that contains pyridine and carbazole, and this material is the material of main part with hole and electron transport ability.
Two of object of the present invention is to provide the preparation method of the bipolar organic material that contains pyridine and carbazole described in a kind of.
The application of the bipolar organic material that contains pyridine and carbazole described in three of object of the present invention is to provide on phosphorescent organic electroluminescent diode.
Technical scheme of the present invention is as follows:
A bipolar organic material that contains pyridine and carbazole, has following chemical structure:
Wherein R
1, R
2, R
3for one of following structural formula:
R
1, R
2, R
3link by covalent linkage and center pyridine nucleus and peripheral carbazole in its optional position.R
1, R
2, R
3structure can be identical, also can be different, but wherein have one at least for six-membered heterocycle.R
4for one of following structural formula:
A preparation method for the bipolar organic material that contains pyridine and carbazole, comprises following concrete steps:
(1) prepare 6-bromo-2 ', 6 '-bis-(3-bromo phenyl)-2,4 '-Lian pyridine: add 6-brominated pyrimidine base formaldehyde, 3-bromoacetophenone, potassium hydroxide, strong aqua and methyl alcohol in nitrogen or argon gas atmosphere downhill reaction bottle, stirring reaction 48 hours under reflux condition; After reaction finishes, naturally cooling, uses chloroform extraction reaction solution; Extraction product column chromatography purification, obtain 6-bromo-2 ', 6 '-bis-(3-bromo phenyl)-2,4 '-Lian pyridines;
(2) prepare 2,6-bis-(3-carbazyl)-phenyl-4-(6-(carbazyl)-2-pyridyl)-pyridine: in nitrogen or argon gas atmosphere downhill reaction bottle, add 6-bromo-2 ', 6 '-bis-(3-bromo phenyl)-2,4 '-Lian pyridine, carbazole, Palladous chloride, tri-tert phosphorus, sodium tert-butoxide and o-Xylol, stirring reaction 12～24 hours under reflux condition; After reaction finishes, naturally cooling, uses chloroform extraction reaction solution; Extraction product column chromatography purification, obtains 2,6-bis-(3-carbazyl)-phenyl-4-(6-(carbazyl)-2-pyridyl)-pyridine.
The above-mentioned bipolar organic material that contains pyridine and carbazole is the application on organic electroluminescent LED luminescent layer as the material of main part of phosphor material.
Compared with prior art, beneficial effect of the present invention for: (1) this bipolar host material is formed by having the pyridine of electron affinity and having to the carbazole unit of electronics, therefore has hole and electron transport ability simultaneously; (2) be applied to the luminescent layer of organic electroluminescent LED as the material of main part of phosphor material, because of its hole and electron-transporting, will effectively promote the balance in hole and electronics in luminescent layer to improve the luminous efficiency of device.(3) as pyridine, the phenyl etc. of Component units each other in a position combination, make this material of main part there is higher triplet, thereby effectively suppress the transfer from phosphor material triplet excitons energy, reduce the non-luminous inactivation of exciton, thereby improve the efficiency of device.(4) between center pyridine nucleus and peripheral carbazole, introduce phenyl or six-membered heterocycle, thereby reach the object of controlled material molecular orbital energy level, singlet and triplet by the quantity of six-membered heterocycle and the adjustment of nitrogen-atoms position thereof.(5) thus improve the charge injection potential barrier of luminescent layer and hole, electron transfer layer interlayer because of the adjustment of material of main part molecular orbital energy level, effectively promote charge injection and transmission to luminescent layer, reduce the driving voltage of device, thereby effectively improve the power efficiency of device.
Brief description of the drawings
Fig. 1 be embodiment mono-prepare 2, uv-visible absorption spectroscopy (ABS) and the fluorescence spectrum (PL) of 6-bis-(3-carbazyl)-phenyl-4-(6-(carbazyl)-2-pyridyl)-pyridine (2) under solid film state.
Fig. 2 be embodiment bis-prepare 2,4, uv-visible absorption spectroscopy (ABS) and the fluorescence spectrum (PL) of 6-tri-(6-(carbazyl)-2-pyridyl)-pyridine (4) under solid film state.
Fig. 3 is current density-luminosity-voltage relationship figure of the green phosphorescent organic electroluminescence device I for preparing of embodiment tri-.
Fig. 4 is power efficiency-external quantum efficiency-luminosity graph of a relation of the green phosphorescent organic electroluminescence device I for preparing of embodiment tri-.
Fig. 5 is current density-luminosity-voltage relationship figure of the red phosphorescent organic electroluminescence device II for preparing of embodiment tri-.
Fig. 6 is power efficiency-external quantum efficiency-luminosity graph of a relation of the red phosphorescent organic electroluminescence device II for preparing of embodiment tri-.
Fig. 7 is the electroluminescent spectrum figure of the green phosphorescent organic electroluminescence device I for preparing of embodiment tri-.
Fig. 8 is the electroluminescent spectrum figure of the red phosphorescent organic electroluminescence device II for preparing of embodiment tri-.
Embodiment
Further illustrate enforcement of the present invention below by specific embodiment, these embodiment (as the consumption of its Raw) are only for example, are not used in and limit the scope of the invention for a person skilled in the art.Embodiment mono-: 2, the preparation of 6-bis-(3-carbazyl)-phenyl-4-(6-(carbazyl)-2-pyridyl)-pyridine (2)
Step I: 6-is bromo-2 ', 6 '-bis-(3-bromo phenyl)-2,4 '-Lian pyridine (1) synthetic
Under nitrogen atmosphere, in 500ml there-necked flask, add 6-brominated pyrimidine base formaldehyde (2.79g, 15mmol), 3-bromoacetophenone (5.97g, 30mmol), potassium hydroxide (0.895g, 16mmol), strong aqua (90ml) and methyl alcohol (300ml), stirring reaction 48 hours under reflux condition.Reaction finishes after naturally cooling, to use chloroform extraction reaction solution, and with saturated common salt water washing 3 times, gained organic layer anhydrous magnesium sulfate drying.Suction filtration, under reduced pressure removes the solvent in gained filtrate.With chromatographic column separation, moving phase used is chloroform/normal hexane=2: 3.After being spin-dried for, vacuum-drying, obtains white powder 1.64g, yield 20%.
1H?NMR(500MHz，CDCl
3)：δ(ppm)8.344(t，J＝1.8Hz，2H)，8.232(s，2H)，8.149-8.128(m，2H)，7.900-7.883(m，1H)，7.733(t，J＝8.0Hz，1H)，7.608-7.586(m，2H)，7.598-7.581(m，1H)，7.406(t，J＝8.0Hz，2H).
13C?NMR(500MHz，CDCl
3)：δ(ppm)156.446，155.870，146.883，142.725，141.035，139.368，132.277，130.312，130.163，128.534，125.803，123.057，119.799，116.881.MS(EI)：m/z?545(calcdm/z?545.06).
Step I i:2,6-bis-(3-carbazyl)-phenyl-4-(6-(carbazyl)-2-pyridyl)-pyridine (2) synthetic
Under nitrogen atmosphere to add in 100ml there-necked flask 6-bromo-2 ', 6 '-bis-(3-bromo phenyl)-2,4 '-Lian pyridine (0.818g, 1.5mmol), carbazole (0.903g, 5.4mmol), Palladous chloride (23.9mg, 0.135mmol), tri-tert phosphorus (109mg, 0.54mmol), sodium tert-butoxide (0.649g, 6.8mmol) and o-Xylol (50ml), stirring reaction 18 hours under reflux condition.Reaction finishes after naturally cooling, to use chloroform extraction reaction solution, and with saturated common salt water washing 3 times, gained organic layer anhydrous magnesium sulfate drying.Suction filtration, under reduced pressure removes the solvent in gained filtrate.With chromatographic column separation, moving phase used is chloroform/normal hexane=1: 1.After being spin-dried for, vacuum-drying, obtains white powder 1.16g, yield 96.1%.
The 1H nuclear magnetic resonance spectrum data of 2,6-bis-(3-carbazyl)-phenyl-4-(6-(carbazyl)-2-pyridyl)-pyridine (2) are as follows:
1H?NMR(500MHz，CDCl
3)：δ(ppm)8.525(s，2H)，8.441(t，J＝2.0Hz，2H)，8.359-8.338(m，2H)，8.172(dd，J＝8.0and?1.0Hz，4H)，8.121-8.103(m，2H)，8.069(t，J＝8.0Hz，1H)，7.977-7.959(m，2H)，7.929(d，J＝8.0Hz，1H)，7.761-7.730(m，3H)，7.665-7.643(m，2H)，7.479-7.463(m，4H)，7.346-7.313(m，4H)，7.300-7.245(m，8H).
13C?NMR(500MHz，CDCl
3)：δ(ppm)157.037，154.257，152.017，147.779，141.195，140.917，139.654，139.299，138.277，130.369，127.928，126.238，126.017，125.918，124.499，123.381，121.275，120.291，120.226，119.971，118.742，117.655，116.740，111.277，109.812.MS(EI)：m/z?804(calcd?m/z?803.95)。
The uv-visible absorption spectroscopy of 2,6-bis-(3-carbazyl)-phenyl-4-(6-(carbazyl)-2-pyridyl)-pyridine (2) under solid film state and fluorescence spectrum are as shown in Figure 1.
Embodiment bis-: 2, the preparation of 4,6-tri-(6-(carbazyl)-2-pyridyl)-pyridine (4)
Synthesizing of step I: 2,4,6-tri-(6-bromo-2-pyridyl base) pyridine (3)
Under nitrogen atmosphere; in 500ml there-necked flask, add 6-brominated pyrimidine base formaldehyde (1.86g; 10mmol), the bromo-2-acetylpyridine of 6-(4.00g; 20mmol), potassium hydroxide (0.561g; 10mmol), strong aqua (60ml) and methyl alcohol (220ml), stirring reaction 63 hours under reflux condition.Reaction finishes after naturally cooling, to use chloroform extraction reaction solution, and with saturated common salt water washing 3 times, gained organic layer anhydrous magnesium sulfate drying.Suction filtration, under reduced pressure removes the solvent in gained filtrate.With chromatographic column separation, moving phase used is chloroform.After being spin-dried for, vacuum-drying, obtains white powder 2.08g, yield 38.1%.
1H?NMR(500MHz，CDCl
3)：δ(ppm)8.969(s，2H)，8.581-8.564(m，2H)，8.018-8.001(m，1H)，7.742(t，J＝8.0Hz，1H)，7.736(t，J＝8.0Hz，2H)，7.597-7.580(m，1H)，7.567-7.550(m，2H).
13C?NMR(500MHz，CDCl
3)：δ(ppm)156.980，156.046，154.836，147.509，142.588，141.718，139.231，139.158，128.433，128.378，120.390，120.070，119.555.MS(EI)：m/z?547(calcd?m/z?547.04)。
Step I i:2,4,6-tri-(6-(carbazyl)-2-pyridyl)-pyridine (4) synthetic
Under nitrogen atmosphere, in 100ml there-necked flask, add 2,4,6-tri-(6-bromo-2-pyridyl base) pyridine (0.438g, 0.80mmol), carbazole (0.482g, 2.88mmol), Palladous chloride (13mg, 0.07mmol), tri-tert phosphorus (58mg, 0.29mmol), sodium tert-butoxide (0.346g, 3.6mmol) and o-Xylol (40ml), stirring reaction 18 hours under reflux condition.Reaction finishes after naturally cooling, to use chloroform extraction reaction solution, and with saturated common salt water washing 3 times, gained organic layer anhydrous magnesium sulfate drying.Suction filtration, under reduced pressure removes the solvent in gained filtrate.With chromatographic column separation, moving phase used is chloroform/normal hexane=2: 1.After being spin-dried for, vacuum-drying, obtains white powder 0.52g, yield 80%.
2,4 of preparation, the 1H nuclear magnetic resonance spectrum data of 6-tri-(6-(carbazyl)-2-pyridyl)-pyridine (4) are as follows:
1H?NMR(500MHz，CDCl
3)：δ(ppm)9.292(s，2H)，8.769(d，J＝8.0and?1.0Hz，2H)，8.179-8.144(m，6H)，8.076-8.061(m，2H)，8.021-7.984(m，5H)，7.945-7.928(m，1H)，7.906-7.889(m，2H)，7.746(dd，J＝8.0and?1.0Hz，2H)，7.674(dd，J＝8.0and?1.0Hz，1H)，7.310-7.276(m，8H)，7.173-7.141(m，2H)，6.969-6.935(m，2H).
13C?NMR(500MHz，CDCl
3)：δ(ppm)156.011，155.962，154.959，152.056，151.323，148.439，139.585，139.521，139.452，139.326，126.249，124.331，121.058，120.993，120.150，119.929，119.204，118.998，118.735，118.513，118.227，111.349，111.311.MS(EI)：m/z?806(calcd?m/z?805.92)。
2,4 of preparation, the uv-visible absorption spectroscopy of 6-tri-(6-(carbazyl)-2-pyridyl)-pyridine (4) under solid film state and fluorescence spectrum are as shown in Figure 2.
Embodiment tri-: bipolar organic material is for the assessment of phosphorescent organic electroluminescent device material of main part
Material is prepared as follows to device architecture and evaluates its performance.Device preparation method is by means known in the art preparations, that is: under high vacuum condition, and evaporation organic materials and cathode electrode successively on the conductive glass ITO cleaning.
Device architecture I:ITO/HIL (20nm)/TAPC (30nm)/above-mentioned materials 2 or 4 and containing 8wt%Ir (PPy)
3(10nm)/ETL (50nm)/LiF (0.5nm)/Al (100nm).
Device architecture II:ITO/HIL (20nm)/TAPC (30nm)/above-mentioned materials 2 or 4 and containing 4wt%Ir (piq)
3(10nm)/ETL (65nm)/LiF (0.5nm)/Al (100nm).
Measured current density-luminosity-voltage relationship the figure of respective devices I as shown in Figure 3.The bright voltage that opens that can find out the device based on material of main part 4 in figure will be lower than the device based on material of main part 2, this is mainly because the introducing of more pyridyl causes the reduction of material lumo energy, makes due to electron transfer layer reduces to the electronic injection obstacle of luminescent layer.Device II also has similar phenomenon (measured current density-luminosity-voltage relationship figure as shown in Figure 5).In power efficiency-external quantum efficiency shown in Fig. 4 and Fig. 6-luminosity graph of a relation, can find out, the device based on material of main part 2 has higher luminous efficiency.In addition, the electroluminescent spectrum basically identical (Fig. 7 and Fig. 8) of the electroluminescent spectrum of the device based on material of main part 2 and the device based on material of main part 4, shows that effective energy shifts from material of main part to phosphor material.
Above content is in conjunction with concrete preferred implementation further description made for the present invention, can not assert that specific embodiment of the invention is confined to these explanations.For general technical staff of the technical field of the invention, without departing from the inventive concept of the premise, its framework form can be flexible and changeable, can subseries product.Just make some simple deduction or replace, all should be considered as belonging to the present invention by the definite scope of patent protection of submitted to claims.
Claims (3)
1. a bipolar organic material that contains pyridine and carbazole, is characterized in that, this compound has following chemical structure:
Wherein R
1, R
2, R
3for one of following structural formula:
And R
1, R
2, R
3link by covalent linkage and center pyridine nucleus and peripheral carbazole in its optional position; R
1, R
2, R
3structure can be identical, also can be different, but wherein have one at least for six-membered heterocycle;
R
4for :-H.
2. according to the preparation method of the bipolar organic material of claim 1, it is characterized in that, comprise the steps:
(1) prepare the bromo-2' of 6-, 6'-bis-(3-bromo phenyl)-2,4'-connects pyridine: in nitrogen or argon gas atmosphere downhill reaction bottle, add 6-brominated pyrimidine base formaldehyde, 3-bromoacetophenone, potassium hydroxide, strong aqua and methyl alcohol, stirring reaction 48 hours under reflux condition; After reaction finishes, naturally cooling, uses chloroform extraction reaction solution; Extraction product column chromatography purification, obtains the bromo-2' of 6-, 6'-bis-(3-bromo phenyl)-2, and 4'-connects pyridine;
(2) prepare 2,6-bis-(3-carbazyl)-phenyl-4-(6-(carbazyl)-2-pyridyl)-pyridine: add the bromo-2' of 6-in nitrogen or argon gas atmosphere downhill reaction bottle, 6'-bis-(3-bromo phenyl)-2,4'-connects pyridine, carbazole, Palladous chloride, tri-tert phosphorus, sodium tert-butoxide and o-Xylol, stirring reaction 12～24 hours under reflux condition; After reaction finishes, naturally cooling, uses chloroform extraction reaction solution; Extraction product column chromatography purification, obtains 2,6-bis-(3-carbazyl)-phenyl-4-(6-(carbazyl)-2-pyridyl)-pyridine.
3. the application of bipolar organic material claimed in claim 1, is characterized in that, this material is applied to the luminescent layer of organic electroluminescent LED as the material of main part of phosphor material.
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| CN103360303B (en) * | 2013-07-31 | 2015-09-16 | 华南理工大学 | A kind of take pyridine as compound of core and its preparation method and application |
| CN104370887B (en) * | 2013-12-26 | 2016-08-24 | 北京阿格蕾雅科技发展有限公司 | The synthetic method of double [3-(N-carbazyl) phenyl] pyridine compounds and their of 2,6- |
| CN105895811B (en) * | 2015-01-26 | 2018-03-20 | 北京维信诺科技有限公司 | A kind of thermal activation sensitized fluorescence organic electroluminescence device |
| KR102653732B1 (en) * | 2018-10-10 | 2024-04-01 | 엘지디스플레이 주식회사 | Organic compounds, organic light emitting diode and organic light emitting device having the compounds |
| TW202114987A (en) | 2019-09-30 | 2021-04-16 | 日商日鐵化學材料股份有限公司 | Organic electroluminescent element |
| TW202122381A (en) * | 2019-09-30 | 2021-06-16 | 日商日鐵化學材料股份有限公司 | Organic electroluminescent element |
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| CN101076528A (en) * | 2004-12-10 | 2007-11-21 | 三菱化学株式会社 | Organic compound, charge transport material and organic electroluminescent element |
| CN102174037A (en) * | 2011-02-28 | 2011-09-07 | 东莞彩显有机发光科技有限公司 | Phosphorescent host material with bipolar carrier transmitting capacity |
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| JP4474493B1 (en) * | 2009-07-31 | 2010-06-02 | 富士フイルム株式会社 | Organic electroluminescence device |
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| CN102174037A (en) * | 2011-02-28 | 2011-09-07 | 东莞彩显有机发光科技有限公司 | Phosphorescent host material with bipolar carrier transmitting capacity |
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