CN104987859A - Organic electrophosphorescence luminescent material, preparation method thereof and luminescent device - Google Patents
Organic electrophosphorescence luminescent material, preparation method thereof and luminescent device Download PDFInfo
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- CN104987859A CN104987859A CN201510350585.4A CN201510350585A CN104987859A CN 104987859 A CN104987859 A CN 104987859A CN 201510350585 A CN201510350585 A CN 201510350585A CN 104987859 A CN104987859 A CN 104987859A
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- 0 CC=CC(C(C1(*)C2=CC=C)*1(ClC)ClC)=C(C)C2=C Chemical compound CC=CC(C(C1(*)C2=CC=C)*1(ClC)ClC)=C(C)C2=C 0.000 description 2
- IMRWILPUOVGIMU-UHFFFAOYSA-N Brc1ncccc1 Chemical compound Brc1ncccc1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- ZLEGTHOLZZOFQA-UHFFFAOYSA-N C1C=CC=CC1c1ccccn1 Chemical compound C1C=CC=CC1c1ccccn1 ZLEGTHOLZZOFQA-UHFFFAOYSA-N 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N OB(c1ccccc1)O Chemical compound OB(c1ccccc1)O HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- GHGZVWOTJDLREY-UHFFFAOYSA-N Oc1ccccc1-c1nc2ccccc2[o]1 Chemical compound Oc1ccccc1-c1nc2ccccc2[o]1 GHGZVWOTJDLREY-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N c(cc1)ccc1-c1ccccn1 Chemical compound c(cc1)ccc1-c1ccccn1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention belongs to ORGANIC ELECTROLUMINESCENCE DISPLAYS technical fields, and in particular to a kind of organic electroluminescent phosphorescence luminescent material and preparation method thereof, and contain organic electroluminescence device of the material as luminescent layer. Technical problem to be solved by the invention is to provide a kind of organic electroluminescent phosphorescence luminescent material and preparation method thereof and using the luminescent device of its preparation, each performance indicator of device of the structural formula of the organic electroluminescent phosphorescence luminescent material such as formula I, material preparation is good.
Description
Technical field
The invention belongs to ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field, be specifically related to a kind of organic electroluminescent phosphorescence luminescent material and preparation method thereof, and containing the organic electroluminescence device of this material as luminescent layer.
Background technology
At present, although be that the flat panel display of main flow is very ripe with lcd technology, still there are some difficulties being difficult to overcome in it.Therefore, in recent years, novel organic electroluminescent is shown one's talent, and becomes technique of display the most popular in flat panel display.Organic electroluminescence device due to the selectivity with material wide, luminous, luminosity and luminous efficiency high, visual angle is wide, fast response time, ultra-thin, lightweight, active illuminating, low in energy consumption, the excellent specific properties such as cost is lower, flat panel display has obvious advantage, obtains extensively research with fast-developing.
As far back as 1963, the electroluminescent of the Pope Late Cambrian monocrystalline anthracene of New York university of the U.S., but due to its driving voltage high, quantum yield is low, fails to cause and studies interest widely.Until 1987, Eastern Kodak company's T ang adopts oxine aluminium successfully to make El element (Tang C W, Vanslyke S A.Appl Phys Lett, 1987, the 51:913 of excellent property; United States Patent (USP), the patent No.: 4356429), the research of organic electroluminescent starts to enter brand-new epoch.Electroluminescent organic material is divided into fluorescent material and phosphor material by the difference of the state that starts of its transition.Theory shows, the ratio of excited triplet state and excited singlet state is 3 ︰ 1, and in fluorescent material, only has 25% for luminescence, and therefore quantum yield is not high.1998, Thompson and Forrest using phosphor material octaethylporphyrin platinum (PtOEP) as luminescent layer, the quantum yield of device is made to break through original restriction, thus open frontier (the Baldo M A of electrophosphorescence, O ' Brien DF.Nature, 1998,395:151).Based on heavy atoms effect, strong Effect of Spin-orbit Coupling can make singlet excited mutually mix with the energy rank of triplet excited state, thus forbidden triplet state can be luminous with phosphorescence form originally.In recent years, containing iridium, platinum, osmium, the phosphor materials such as copper are extensively studied, and wherein because the stability of compounds of iridium, good luminous performance, under study for action in occupation of consequence.
In order to meet the full-color display of display device, generally need to use ruddiness, green glow and blue light.The saturation ratio of device can be improved owing to adding gold-tinted in the devices, therefore, substitute with yellow green light the raising that green glow effectively can realize device performance.Therefore, yellow green light developing material has actual application value, but the research of yellow green light organic electroluminescent phosphorescence luminescent material is also very weak at present, and this area needs suitable yellow green light organic electroluminescent phosphorescence luminescent material for preparing organic electroluminescence device.
Summary of the invention
First technical problem to be solved by this invention is to provide a kind of yellow green light organic electroluminescent phosphorescence luminescent material, and this material is for structural formula is such as formula the compound shown in I:
Lr in formula I represents iridium Iridium.This compound can close iridium by called after benzoxazolyl-phenoxy group two (2-phenylpyridine-C2, N), and its English name can be abbreviated as Ir (ppy)
2bop.
Second technical problem to be solved by this invention is to provide the preparation method of above-mentioned yellow green light organic electroluminescent phosphorescence luminescent material.
The method comprises the following steps:
A, under an inert gas, by 2-bromopyridine or 2-iodine pyridine and phenyl-boron dihydroxide, 1 ~ 1.5 ︰ 1 and palladium catalyst are dissolved in solvent in molar ratio, add in sodium carbonate, salt of wormwood or cesium carbonate again any one, carry out suzuki reaction, back flow reaction 8 ~ 24h, cooling, purifies, obtains 2-phenylpyridine;
B, under an inert atmosphere, 2-phenylpyridine and three hydrated iridium trichloride are dissolved in solvent with mol ratio 2 ~ 3:1, back flow reaction 8 ~ 24h, cooling, purify, obtain intermediate dimerization iridium complex;
C, under an inert gas, by intermediate dimerization iridium complex and 2-, (2-hydroxyphenyl) benzoxazole is dissolved in glycol dimethyl ether with mol ratio 1 ︰ 2 ~ 1:4, add sodium carbonate and form alkaline condition, carry out ligand exchange reaction, back flow reaction 8 ~ 24h, purify, obtain compound shown in formula I.
Wherein, the solvent described in aforesaid method step a is toluene, DMF, Isosorbide-5-Nitrae-dioxane or volume ratio be any one in the toluene of 2 ︰ 1 and the mixing solutions of ethanol.
Wherein, the palladium catalyst described in the rapid a of above-mentioned measured step is tetra-triphenylphosphine palladium or two (triphenylphosphine) palladium chloride, and the molar weight that palladium catalyst adds is add by 0.001 ~ 0.005 times of molar weight of 2-bromopyridine or 2-iodine pyridine.
Wherein, the solvent described in aforesaid method step b is the glycol dimethyl ether of volume ratio 2 ︰ 1 and the mixing solutions of water.
Wherein, in aforesaid method step a, described purification is: merge organic phase with dichloromethane extraction after system is concentrated, washing organic phase, anhydrous magnesium sulfate drying organic phase, filters, removing methylene dichloride, silica gel column chromatography is separated and obtains compound 2-phenylpyridine.
Wherein, the purification described in aforesaid method step b is: filter and obtain the precipitation cooling rear precipitation, and washing solid, obtains intermediate dimerization iridium complex.
Wherein the purification described in aforesaid method step c is: after system is concentrated, merges organic phase, washing organic phase with dichloromethane extraction, anhydrous magnesium sulfate drying organic phase, filter, removing methylene dichloride, more namely obtain compound shown in formula I with tetrahydrofuran (THF) recrystallization.
3rd technical problem to be solved by this invention is to provide the above-mentioned organic electroluminescence device prepared by organic electroluminescent phosphorescence luminescent material.This organic electroluminescence device be with compound shown in formula I for electroluminescent raw material, can prepare by this area common method.Such as, the method for conventional vacuum evaporation can be used to carry out the preparation of each layer.The compounds of this invention is when preparing organic electroluminescence device, and as the doping object in luminescent layer, it is luminous that effect is to excite phosphorescence.
Further, a typical structure of above-mentioned organic electroluminescence device is the glass substrate/ITO/MoO3/TAPC/CBP:Ir (ppy) of lamination successively
2bop/TPBi/LiF/Al.This structure is easily obtained by the method for vacuum evaporation on a glass substrate.
Beneficial effect of the present invention is by the modification to Ir complex compound, creatively have employed new assistant ligand, obtain a kind of efficient yellow green light luminescent material completely newly, this compound is launched as being entrained in the yellow green light that can obtain efficient stable in organic electroluminescence device luminescent layer for guest materials, and the organic luminescent device utilizing the compounds of this invention to prepare shows high brightness, high efficiency excellent properties.Luminous organic material of the present invention can provide the material of the yellow green light needed for white light parts, and its luminescent quality is good, and efficiency is high; And preparation method is simple, is applicable to a large amount of production, is with a wide range of applications.
Accompanying drawing explanation
Fig. 1 is the structural representation of the organic electroluminescence device of embodiment.
Fig. 2 is the utilizing emitted light spectrogram of the electroluminescent material of embodiment.
Embodiment
Main thought of the present invention is by the modification of compound and adjustment, the luminescence realizing material with or without and emission wavelength and quantum yield are regulated, obtain suitable material.On a large amount of Research foundations, we wish, by conjunction with different assistant ligands, to changing the energy of MLCT charge transfer, and then to change the HOMO energy level of iridic compound molecule.Finally utilize to have and obtain novel iridic compound to the assistant ligand of Electronic Performance benzoxazolyl-phenoxy group (2-(benzo [d] oxazol-2-yl) phenol (bop)) synthesis.This iridic compound is a kind of dopant material of the novel green glow that can turn to be yellow, its structural formula following I:
And the typical synthetic route of the preparation of above-mentioned organic electroluminescent phosphorescence luminescent material, available following reaction equation represents:
Compound in above-mentioned reaction formula
A is 2-bromopyridine, also can use 2-iodine pyridine;
B is phenyl-boron dihydroxide;
C is 2-phenylpyridine;
D is dimerization iridium complex intermediate;
E is 2-(2-hydroxyphenyl) benzoxazole.
Specifically the compounds of this invention can obtain by concrete grammar below:
A, under an inert gas, compd A and compd B are dissolved in solvent with mol ratio 1.5 ︰ 1 and palladium catalyst, then add sodium carbonate, back flow reaction 24h, cooling, purify, obtain Compound C; Described solvent is the toluene of volume ratio 2 ︰ 1 and the mixing solutions of ethanol; Described palladium catalyst is tetra-triphenylphosphine palladium; The addition of described sodium carbonate is the twice of compd B;
B, under an inert gas, Compound C and three hydrated iridium trichloride are dissolved in solvent with mol ratio 2.35 ︰ 1, back flow reaction 24h, cooling, purify, obtain dimerization iridium complex intermediate; Described solvent is the glycol dimethyl ether of volume ratio 2 ︰ 1 and the mixing solutions of water;
C, under an inert gas, dimerization iridium complex intermediate and compd E are dissolved in solvent with mol ratio 1 ︰ 2 ~ 4, after adding sodium carbonate reaction, organic electromechanical phosphorescent material I can be obtained; Described solvent is glycol dimethyl ether.
Concrete, in the preparation method step a of above-mentioned organic electroluminescent phosphorescence luminescent material, described purification is: concentrating under reduced pressure, organic phase is merged, washing organic phase, anhydrous magnesium sulfate drying organic phase with dichloromethane extraction, filter, removing methylene dichloride, silica gel column chromatography is separated and obtains Compound C.
Concrete, in the preparation method step b of above-mentioned organic electroluminescent phosphorescence luminescent material, described purification is: the precipitation separated out after filtering cooling, and washing solid, obtains dimerization iridium complex intermediate.
Concrete, the preparation method of above-mentioned organic electroluminescent phosphorescence luminescent material, in step c, described purification is: concentrating under reduced pressure, merges organic phase with dichloromethane extraction, washing organic phase, anhydrous magnesium sulfate drying organic phase, filter, removing methylene dichloride, more namely obtain the compound shown in formula I with tetrahydrofuran (THF) recrystallization.
The preparation of embodiment one organic electroluminescent phosphorescence luminescent material of the present invention
A, in 250mL twoport round-bottomed flask, add 4.74g 2-bromopyridine, 2.44g phenyl-boron dihydroxide, tetra-triphenylphosphine palladium 0.1g (catalyzer), 30mL toluene, 15mL ethanol, 20mL concentration is the sodium carbonate solution of 2mol/L, under the protection of nitrogen at 110 DEG C stirring reaction 24h; After reaction terminates, question response liquid is cooled to room temperature, repeatedly uses methylene dichloride separatory, merges all organic phases, utilizes pillar layer separation, and dry, obtain the 2-phenylpyridine of 2.56g, productive rate is 85%;
B, the 2-phenylpyridine adding 2.56g in 250mL twoport round-bottomed flask and 2.1g tri-hydrated iridium trichloride, 80mL glycol dimethyl ether and 40mL water, in stirred under reflux temperature reaction 24h under the protection of nitrogen; After reaction terminates, question response liquid is cooled to room temperature, suction filtration, and solid is washed, dry, obtains 1.86g containing iridium intermediate; This thick finished product need not be purified further, can be directly used in next step reaction;
C, in 100mL twoport round-bottomed flask, add that 1.07g step b obtains containing iridium intermediate, 0.63g 2-(2-hydroxyphenyl) benzoxazole, 1.5g sodium carbonate, 50mL glycol dimethyl ether; Stirring reaction 24h under reflux temperature under the provide protection of nitrogen; After reaction terminates, question response liquid is cooled to room temperature, suction filtration, and by gained solid tetrahydrofuran (THF) recrystallization, obtain 0.97g electroluminescent organic material Ir (ppy) 2bop, productive rate is 68%.
The master equation of the present embodiment is:
It is as follows that the product organic electroluminescent phosphorescence luminescent material that the present embodiment obtains detects data:
Mass spectrum (m/z): 711.2 (M+), Theoretical Calculation: C
35h
24irN
3o
2: 710.
Ultimate analysis: C
35h
24irN
3o
2
Theoretical value (%): C, 59.14; H, 3.4; N:5.9.
Measured value (%): C, 59.45; H, 3.82; N, 5.56.
Testing identity, obtains the compound shown in formula I.
Embodiment 2 prepares organic electroluminescence device
Organic electroluminescence device internal structure order prepared by this example is: anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, negative electrode.
As shown in Figure 1, this device comprises the glass substrate/ITO/MoO3/TAPC/CBP:Ir (ppy) of lamination successively to the organic electroluminescence device structure of the present embodiment
2bop/TPBi/LiF/Al.(glass substrate/tin indium oxide/molybdenum oxide/4,4'-cyclohexyl two [N, N-bis-(4-aminomethyl phenyl) aniline]/4,4-bis-(9-carbazole) biphenyl: benzoxazolyl-phenoxy group two (2-phenylpyridine-C2, N) iridium/1 is closed, 3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene/lithium fluoride/aluminium).
The present embodiment organic electroluminescence device can be prepared with reference to the various vacuum vapour depositions that this area is conventional.
Also can following methods be specifically adopted to prepare: on the glass substrate that ITO (tin indium oxide) film that is cleaned and that cross by ozonize covers, pass through vacuum evaporation technology, when not destroying vacuum, on ITO, evaporation thickness is that the MoO3 of 0.5nm is as hole injection layer successively; Thickness is that the TAPC of 40nm is as hole transmission layer; To be 30nm close the CBP of iridium as luminescent layer doped with the benzoxazolyl-phenoxy group two (2-phenylpyridine-C2, N) of 8%wt (mass percent) to thickness; Thickness is that 40nm TPBi is as electron transfer layer; Thickness is that the LiF of 1nm is as electron injection buffer layer; On last evaporation, the Al of 120nm is as device cathodes, and the structure of this device is see Fig. 1.This example prepares light-emitting area and is about 0.1cm
2sample)
The main performance index of the present embodiment obtained device is in table 1:
The main performance index of table 1 obtained device
Can find out, organic electromechanical phosphorescent material provided by the present invention can be used for preparing high-performance, high efficiency doping electro phosphorescent device, and especially its maximum power efficiency index is greater than like product, for electromechanical phosphorescent material provides new selection.
Claims (10)
1. organic electroluminescent phosphorescence luminescent material, is characterized in that: for structural formula is such as formula the compound shown in I:
2. the preparation method of organic electroluminescent phosphorescence luminescent material according to claim 1, is characterized in that: comprise the following steps:
A, under an inert gas, by 2-bromopyridine or 2-iodine pyridine and phenyl-boron dihydroxide, 1 ~ 1.5 ︰ 1 and palladium catalyst are dissolved in solvent in molar ratio, add in sodium carbonate, salt of wormwood or cesium carbonate again any one, carry out suzuki reaction, back flow reaction 8 ~ 24h, cooling, purifies, obtains 2-phenylpyridine;
B, under an inert atmosphere, be dissolved in solvent, back flow reaction 8 ~ 24h by 2-phenylpyridine and three hydrated iridium trichloride with mol ratio 2 ~ 3:1, cooling, the precipitation separated out of purifying, obtains intermediate dimerization iridium complex;
C, under an inert gas, by intermediate dimerization iridium complex and 2-, (2-hydroxyphenyl) benzoxazole is dissolved in glycol dimethyl ether with mol ratio 1 ︰ 2 ~ 1:4, add sodium carbonate and form alkaline condition, carry out ligand exchange reaction, after back flow reaction 8 ~ 24h, compound shown in formula I of purifying to obtain.
3. method according to claim 2, is characterized in that: the solvent described in step a is toluene, DMF, Isosorbide-5-Nitrae-dioxane or volume ratio are the toluene of 2 ︰ 1 and any one in the mixing solutions of ethanol.
4. method according to claim 2, it is characterized in that, palladium catalyst described in step a is tetra-triphenylphosphine palladium or two (triphenylphosphine) palladium chloride, and the add-on of palladium catalyst is add by 0.001 ~ 0.005 times of molar weight of 2-bromopyridine or 2-iodine pyridine.
5. method according to claim 2, is characterized in that: the glycol dimethyl ether of the solvent volume described in step b than 2 ︰ 1 and the mixing solutions of water.
6. the preparation method of organic electroluminescent phosphorescence luminescent material according to claim 2, it is characterized in that: in step a, described purification is: merge organic phase with dichloromethane extraction after system is concentrated, washing organic phase, anhydrous magnesium sulfate drying organic phase, filter, removing methylene dichloride, silica gel column chromatography is separated and obtains compound 2-phenylpyridine.
7. the preparation method of organic electroluminescent phosphorescence luminescent material according to claim 2, is characterized in that: the purification described in step b is: filter and obtain the precipitation cooling rear precipitation, and washing solid, obtains intermediate dimerization iridium complex.
8. the preparation method of organic electroluminescent phosphorescence luminescent material according to claim 2, it is characterized in that: in step c, described purification is: after system is concentrated, organic phase is merged with dichloromethane extraction, washing organic phase, anhydrous magnesium sulfate drying organic phase, filters, removing methylene dichloride, more namely obtain compound shown in formula I with tetrahydrofuran (THF) recrystallization.
9. be the organic electroluminescence device that raw material prepares by organic electroluminescent phosphorescence luminescent material according to claim 1.
10. organic electroluminescence device according to claim 9, is characterized in that: its structure is the glass substrate/ITO/MoO3/TAPC/CBP:Ir (ppy) of lamination successively
2bop/TPBi/LiF/Al.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1705730A (en) * | 2001-11-07 | 2005-12-07 | E·I·内穆尔杜邦公司 | Electroluminescent iridium compounds having red-orange or red emission and devices made with such compounds |
| CN101263151A (en) * | 2005-09-12 | 2008-09-10 | 新日铁化学株式会社 | Process for production of ortho-metallized complex of iridium with homoligand |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1705730A (en) * | 2001-11-07 | 2005-12-07 | E·I·内穆尔杜邦公司 | Electroluminescent iridium compounds having red-orange or red emission and devices made with such compounds |
| CN101263151A (en) * | 2005-09-12 | 2008-09-10 | 新日铁化学株式会社 | Process for production of ortho-metallized complex of iridium with homoligand |
Non-Patent Citations (2)
| Title |
|---|
| HYE RIM PARK ET AL.: "Luminescence Color Tuning of the Iridium Complexes by Interligand Energy Transfer(ILET) with Ancillary Ligands for Organic Light Emitting Diode", 《JOURNAL OF NANOSCIENCE AND NANOTECHNOLOGY》 * |
| YI LIU ET AL.: "Phosphorescent Iridium(III) Complex with an N^O Ligand as a Hg2+-Selective Chemodosimeter and Logic Gate", 《INORGANIC CHEMISTRY》 * |
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