CN102391301B - Phosphorescent main body material - Google Patents
Phosphorescent main body material Download PDFInfo
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- CN102391301B CN102391301B CN201110263028.0A CN201110263028A CN102391301B CN 102391301 B CN102391301 B CN 102391301B CN 201110263028 A CN201110263028 A CN 201110263028A CN 102391301 B CN102391301 B CN 102391301B
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Abstract
The invention discloses a phosphorescent main body material which simultaneously has a high triplet state energy level and a bipolar carrier transport property, and not only contains diphenylamine or a diphenylamine unit Dn derived from a methoxy group with a hole transport property, but also contains triazole, diphenylphosphine oxide or a pyridine unit An with an electron transport property, wherein the diphenylamine unit Dn and the pyridine unit An are connected by using tetraarysilane as a bridge. The structure is shown as the following formula. The synthesis method of the main body material disclosed by the invention is simple and feasible and the application is wide. An electrophosphorescent device made of the main body material has electroluminescent properties such as high efficiency, high brightness and low efficiency attenuation, and can be widely used in the organic electroluminescent field.
Description
technical field
The present invention relates to a kind of phosphorescence bipolar carrier transmission material of main part and in the application in electroluminescent field, belong to field of light emitting materials.
Background technology
From people's reported first such as the C. W. Tang of Kodak in 1987, by vacuum deposition method, prepare with Alq
3since bi-layer devices structure for luminescent material, organic electroluminescent has just obtained people's very big concern.Organic electroluminescent can be divided into fluorescence and phosphorescence electroluminescent, and the electroluminescent of phosphor material can utilize the energy of whole excitons, has larger superiority.
In present electrophosphorescence device, mostly adopt Subjective and Objective structure, soon phosphorescent emissions material, with certain doped in concentrations profiled in main substance, to avoid burying in oblivion of concentration quenching and triplet state-triplet state, improves phosphorescent emissions efficiency.
Forrest in 2003 and Thompson etc. (R. J. Holmes, S. R. Forrest, Y.-J. Tung, R. C. Kwong, J. J. Brown, S. Garon, M E Thompson,
appl. Phys. Lett. 2003, 82,2422) by sky blue phosphor material FIrpic with the doped in concentrations profiled of 6 wt% at 3,5-
n,
nin the material of main part of '-bis-carbazoles-benzene (mCP), the maximum external quantum efficiency of the blue light OLED of acquisition reaches 7.5%, and power efficiency reaches 7.9 lm/W.
Forrest in 2003 and Thompson etc. (R. J. Holmes, B. W. D'Andrade, S. R. Forrest, X. Ren, J. Li, M. E. Thompson,
appl. Phys. Lett. 2003, 83,3818) by dark blue smooth phosphor material FIr6 with the doped in concentrations profiled of 10 wt% in the material of main part of p-two (triphenyl is silica-based) benzene (UGH2), the maximum external quantum efficiency of the device of acquisition reaches 11.6%, power efficiency reaches 13.9 lm/W.
Tokito in 2003 etc. (S. Tokito, T. Iijima, Y. Suzuri, H. Kita, T. Tsuzuki, F. Sato,
appl. Phys. Lett. 2003, 83,569) and FIrpic is entrained in to 4,4 '-bis-(9-carbazoles)-2,2 '-dimethyl-biphenyl, obtains the maximum external quantum efficiency of device and reaches 10.4%, and power efficiency reaches 10.5 lm/W.
In recent years, the electrophosphorescence device of green glow and ruddiness has obtained and can be used in practical high-level efficiency; Yet the development of day blue light and dark blue photoelectricity photo-phosphorescence relatively lags behind.Wherein, one of important reason is to lack the material of main part simultaneously with high triplet and bipolar carrier transmission performance.
Summary of the invention
The problem to be solved in the present invention is for the deficiencies in the prior art, and a kind of phosphorescent light body material simultaneously with high triplet and bipolar carrier transmission performance is provided.
The technical solution used in the present invention is: a kind of electrophosphorescence material of main part, comprise the cells D n with hole transport performance and the unit An with electronic transmission performance, the unit with hole transport performance and the unit with electronic transmission performance are connected by take the mode that four aryl silicon are bridge, and structure is shown below:
1
Wherein,
d n for
a n for
Above-mentioned materials can be as the main body of phosphor material in electroluminescent.
The invention still further relates to a kind of electroluminescent device, comprise glass, be attached to Conducting Glass layer on glass, the hole injection layer closing with Conducting Glass laminating, hole transmission layer with hole injection layer laminating, electronic barrier layer with hole transmission layer laminating, luminescent layer with electronic barrier layer laminating, electron transfer layer with luminescent layer laminating, cathode layer with electron transfer layer laminating, luminescent layer is comprised of material of main part and dopant material, the material of main part of luminescent layer is the described compound of formula (1), dopant material is the common complex of iridium with cyclic metal complexes, as the FIr6 that sends out light dark blue, send out the FIrpic of day blue light, the Ir of green glow (ppy)
2or the Ir (fbi) that sends out light orange (acac)
2(acac).Complex doped ratio (dopant material/all material): FIr6 is 10 wt%, and FIrpic is 8 wt%, Ir (ppy)
2(acac) be 9 wt%, Ir (fbi)
2(acac) be 8 wt%.
Material of main part of the present invention is applied in electro phosphorescent device, can obtain efficient electroluminescent properties.The blue light electro phosphorescent device that FIr6 is prepared as object is take in the present invention, and high-high brightness reaches every square metre of 10338 Kan Tela, and maximum luminous efficiency can reach every ampere of 35.8 Kan Tela, is that the dark blue optical device effect of current single-shot photosphere is one of best; The blue light electro phosphorescent device that the FIrpic of take is prepared as object, high-high brightness reaches every square metre of 14837 Kan Tela, and maximum luminous efficiency can reach every ampere of 40.9 Kan Tela, approaches the most effective value of current single-shot photosphere device current; With Ir (ppy)
2(acac) the green glow electro phosphorescent device of preparing for object, high-high brightness reaches every square metre of 47987 Kan Tela, and maximum luminous efficiency can reach every ampere of 86.0 Kan Tela, is that current single-shot photosphere device effect is one of best; With Ir (fbi)
2(acac) the orange photoelectricity phosphorescent device that prepared by object, high-high brightness reaches every square metre of 43405 Kan Tela, and maximum luminous efficiency can reach every ampere of 51.6 Kan Tela, is that similar device performance is best.As can be seen here, the present invention has useful technique effect.
Accompanying drawing explanation
Fig. 1 embodiment of the present invention 1 gained material of main part 4-{4-[5-(4-tert-butyl-phenyl)-hydrogen-1,4-phenyl-4,2,4-triazole-3-] phenyl-phenylbenzene silicon } the uv-visible absorption spectra figure of phenyl-pentanoic;
Fig. 2 embodiment of the present invention 1 gained material of main part 4-{4-[5-(4-tert-butyl-phenyl)-hydrogen-1,4-phenyl-4,2,4-triazole-3-] phenyl-phenylbenzene silicon } the photoluminescence figure of phenyl-pentanoic;
Fig. 3 EL device structure schematic diagram of the present invention;
The emmission spectrum of Fig. 4 electroluminescent device of the present invention.
Embodiment
Below by specific embodiment, the present invention is further illustrated, and its object is to help better to understand content of the present invention, but the protection domain that these specific embodiments do not limit the present invention in any way.The present embodiment raw material used is known compound, can on market, buy, or available methods known in the art is synthetic.
4-{4-[5-(4-tert-butyl-phenyl)-hydrogen-1,4-phenyl-4,2,4-triazole-3-] phenyl-phenylbenzene silicon } preparation of phenyl-pentanoic (be abbreviated as Host1, structural formula is as follows)
By 2.07 grams of 3-[4-(4-bromophenyl-phenylbenzene silicon) phenyl]-5-(4-tert-butyl-phenyl)-hydrogen-1,4-phenyl-4, 2, 4-triazole, 0.54 gram of pentanoic, 13.5 milligram palladium, 52.2 milligrams of tri-tert phosphorus a tetrafluoro borates and 0.35 gram of sodium tert-butoxide add in 50 ml flasks, add 20 milliliters of toluene, under argon shield, reflux 18 hours, after cooling, pour in saturated aqueous ammonium chloride, dichloromethane extraction, salt water washing, anhydrous sodium sulfate drying, filter, be spin-dried for, thick ethyl acetate/dichloromethane=1:15 (v/v) column chromatography for product, be spin-dried for and obtain product.Productive rate 45%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?7.53-7.48?(m,?6H),?7.46-7.40?(m,?6H),?7.38-7.29?(m,?11H),?7.24-7.19?(m,?6H),?7.13?(d,?
J?=?7.2?Hz,?4H),?7.07-7.00?(m,?4H),?1.28?(s,?9H)。MS?(EI):?m/z?778.3?[M
+]。
4-[(4-pyridine-3-phenyl)-phenylbenzene silicon] preparation of phenyl pentanoic (be abbreviated as Host2, structural formula is as follows)
By 2.04 grams of 4-(4-bromophenyl-phenylbenzene silicon) phenyl pentanoic; 0.49 gram of 3-pyridine boric acid; 80 milligram of four (triphenyl phosphorus) palladium adds in 100 ml flasks; the solution of potassium carbonate of 7 milliliters 2 moles every liter that adds successively deoxygenation in advance; 35 milliliters of toluene and 8 milliliters of ethanol; under argon shield, reflux 48 hours; after cooling, pour in saturated aqueous common salt; dichloromethane extraction, salt water washing, anhydrous sodium sulfate drying; filter; be spin-dried for, thick ethyl acetate/dichloromethane=1:10 (v/v) column chromatography for product, is spin-dried for and obtains product.Productive rate 59%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?8.88?(s,?1H),?8.60?(s,?1H),?7.91?(d,?
J?=?7.5?Hz,?1H),?7.70?(d,?
J?=?7.8?Hz,?2H),?7.61-7.59?(m,?5H),?7.43-7.37?(m,?8H),?7.29-7.24?(m,?6H),?7.14?(d,?
J?=?7.8?Hz,?4H),?7.05-7.04?(m,?4H)。MS?(EI):?
m/z?580.4?[M
+]。
4-[4-(diphenylphosphine oxygen) phenyl-phenylbenzene silicon] preparation of phenyl pentanoic (be abbreviated as Host3, structural formula is as follows)
1.96 grams of 4-(4-bromophenyl-phenylbenzene silicon) phenyl pentanoic is dissolved in to 50 milliliters of anhydrous tetrahydro furans in 100 milliliters of low-temp reaction bottles, in-78
oafter cooling under C, slowly drip wherein the n-butyllithium solution of 1.8 milliliters 2.26 moles every liter, after dripping in-78
ounder C, react 2 hours.Then slowly add wherein 0.86 milliliter of diphenyl phosphorus chloride, then in-78
ounder C, react 1 hour, slowly rise to ambient temperature overnight.Reaction finishes the rear saturated aqueous common salt cancellation of using, and steams most of tetrahydrofuran (THF), dichloromethane extraction, and salt water washing, anhydrous sodium sulfate drying, filters, and is spin-dried for.Thick product is dissolved with 20 milliliters of methylene dichloride, carefully add the hydrogen peroxide of 8 milliliters of 30wt%, normal-temperature reaction 8 hours, separates organic phase, with salt water washing for several times, anhydrous sodium sulfate drying, filters, be spin-dried for, with ethanol/methylene=1:30 (v/v) column chromatography, be spin-dried for and obtain product.Productive rate 45%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?7.71-7.62?(m,?8H),?7.56-7.54?(m,?6H),?7.48-7.43?(m,?5H),?7.41-7.34?(m,?7H),?7.29-7.24?(m,?4H),?7.13?(d,?
J?=?7.8?Hz,?4H),?7.07-7.01?(m,?4H)。MS?(EI):?
m/z?703.4?[M
+]。
4-{4-[5-(4-tert-butyl-phenyl)-hydrogen-1,4-phenyl-4,2,4-triazole-3-] phenyl-phenylbenzene silicon } preparation of phenyl-bis-(4-p-methoxy-phenyl) amine (be abbreviated as Host4, structural formula is as follows)
By 2.07 grams of 3-[4-(4-bromophenyl-phenylbenzene silicon) phenyl]-5-(4-tert-butyl-phenyl)-hydrogen-1,4-phenyl-4, 2, 4-triazole, 0.73 gram of two (4-p-methoxy-phenyl) amine, 13.5 milligram palladium, 52.2 milligrams of tri-tert phosphorus a tetrafluoro borates and 0.35 gram of sodium tert-butoxide add in 50 ml flasks, add 20 milliliters of toluene, under argon shield, reflux 18 hours, after cooling, pour in saturated aqueous ammonium chloride, dichloromethane extraction, salt water washing, anhydrous sodium sulfate drying, filter, be spin-dried for, thick ethyl acetate/dichloromethane=1:15 (v/v) column chromatography for product, be spin-dried for and obtain product.Productive rate 53%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?7.50-7.41?(m,?14H),?7.37-7.34?(m,?6H),?7.30-7.25?(m,?5H),?7.22-7.18?(m,?2H),?7.09?(d,?J?=?8.4?Hz,?4H),?6.85-6.82?(m,?4H),?3.79?(s,?6H),?1.28?(s,?9H)。MS?(EI):?m/z?838.6?[M
+]。
4-[(4-pyridine-3-phenyl)-phenylbenzene silicon] preparation of phenyl-bis-(4-p-methoxy-phenyl) amine (be abbreviated as Host5, structural formula is as follows)
By 2.24 grams of 4-(4-bromophenyl-phenylbenzene silicon) phenyl-bis-(4-p-methoxy-phenyl) amine; 0.49 gram of 3-pyridine boric acid; 80 milligram of four (triphenyl phosphorus) palladium adds in 100 ml flasks; the solution of potassium carbonate of 7 milliliters 2 moles every liter that adds successively deoxygenation in advance; 35 milliliters of toluene and 8 milliliters of ethanol; under argon shield, reflux 48 hours; after cooling, pour in saturated aqueous common salt; dichloromethane extraction, salt water washing, anhydrous sodium sulfate drying; filter; be spin-dried for, thick ethyl acetate/dichloromethane=1:10 (v/v) column chromatography for product, is spin-dried for and obtains product.Productive rate 75%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?8.87?(s,?1H),?8.61?(s,?1H),?7.90?(d,?
J?=?7.5?Hz,?1H),?7.68?(d,?
J?=?7.8?Hz,?2H),?7.62-7.58?(m,?5H),?7.45-7.38?(m,?6H),?7.30-7.22?(m,?6H),?7.14?(d,?
J?=?7.8?Hz,?4H),?6.92-6.82?(m,?4H),?3.78?(s,?6H)。MS?(EI):?
m/z?640.3?[M
+]。
4-[4-(diphenylphosphine oxygen) phenyl-phenylbenzene silicon] preparation of phenyl-bis-(4-p-methoxy-phenyl) amine (be abbreviated as Host6, structural formula is as follows)
2.15 grams of 4-(4-bromophenyl-phenylbenzene silicon) phenyl-bis-(4-p-methoxy-phenyl) amine is dissolved in to 50 milliliters of anhydrous tetrahydro furans in 100 milliliters of low-temp reaction bottles, in-78
oafter cooling under C, slowly drip wherein the n-butyllithium solution of 1.8 milliliters 2.26 moles every liter, after dripping in-78
ounder C, react 2 hours.Then slowly add wherein 0.86 milliliter of diphenyl phosphorus chloride, then in-78
ounder C, react 1 hour, slowly rise to ambient temperature overnight.Reaction finishes the rear saturated aqueous common salt cancellation of using, and steams most of tetrahydrofuran (THF), dichloromethane extraction, and salt water washing, anhydrous sodium sulfate drying, filters, and is spin-dried for.Thick product is dissolved with 20 milliliters of methylene dichloride, carefully add the hydrogen peroxide of 8 milliliters of 30wt%, normal-temperature reaction 8 hours, separates organic phase, with salt water washing for several times, anhydrous sodium sulfate drying, filters, be spin-dried for, with ethanol/methylene=1:30 (v/v) column chromatography, be spin-dried for and obtain product.Productive rate 43%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?7.73-7.64?(m,?8H),?7.58-7.53?(m,?6H),?7.49-7.44?(m,?4H),?7.42-7.33?(m,?6H),?7.30-7.26?(m,?4H),?7.15?(d,?
J?=?7.8?Hz,?4H),?6.85-6.79?(m,?4H),?3.81?(s,?6H)。MS?(EI):?
m/z?763.6?[M
+]。
The preparation of embodiment 7 electro phosphorescent devices
As shown in Figure 3, bipolar carrier transmission material of the present invention, as the electro phosphorescent device of luminescent layer main body, comprises glass and conductive glass (ITO) substrate layer 1, hole injection layer 2(molybdic oxide MoO
3), hole transmission layer 3(4,4 '-bis-(
n-phenyl-
n-Nai Ji)-biphenyl NPB), electronic barrier layer 4(4,4 ', 4 ' '-tri-(N-carbazole) triphenylamine TCTA) the prepared material of main part doping of luminescent layer 5(embodiment 1 ~ 6 phosphorescent iridium complex), electron transfer layer 6(1,3,5-tri-(N-phenyl benzimidazolyl-2 radicals-) benzene TPBI), cathode layer 7(lithium fluoride/aluminium).
Electroluminescent device is made by means known in the art, as press reference (
adv. Mater.2004,
16, 537.) and disclosed method making.Concrete grammar is: under high vacuum condition, and the MoO of evaporation 10nm successively on conductive glass (ITO) substrate through cleaning
3, the NPB of 80nm, the TCTA of 5 nm, the luminescent layer of 20 nm, the TPBI of 40nm, the LiF of 1nm and the Al of 100nm.By the method, make device as shown in Figure 3, the structure of various devices is as follows:
Device 1 (D1):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host1:FIr6(10wt%,20nm)/TPBI(40nm)/LiF(1nm)/Al(100nm)
Device 2 (D2):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host4:FIrpic(8wt%,20nm)/TPBI(40?nm)/
LiF(1nm)/Al(100nm)
Device 3 (D3):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host2:FIr6(10wt%,20nm)/TPBI(40?nm)/
LiF(1nm)/Al(100nm)
Device 4 (D4):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host5:FIrpic(8wt%,20nm)/TPBI(40nm)/LiF(1nm)/Al(100nm)
Device 5 (D5):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host3:Ir(ppy)
2(acac)(9wt%,20nm)/TPBI(40?nm)/LiF(1nm)/Al(100nm)
Device 6 (D6):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host6:Ir(fbi)
2(acac)(8wt%,20nm)/TPBI(40?nm)/LiF(1nm)/Al(100nm)
Electric current-the brightness-voltage characteristic of device is to be completed by the Keithley source measuring system with corrected silicon photoelectric diode (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter), electroluminescent spectrum is by the French JY SPEX CCD3000 of company spectrometer measurement, and all measurements all complete in atmosphere at room temperature.The performance data of device sees the following form:
The dark blue light of device 1 transmitting of preparation, electroluminescent properties far away higher than documents (
appl. Phys. Lett. 2003, 83,3818), its maximum current efficiency reaches 35.8 cd/A, and maximum power efficiency reaches 34.2 lm/W, is that the dark blue optical device effect of single-shot photosphere is one of best; Device 2 transmitting day blue lights for preparation, electroluminescent properties also higher than documents (
appl Phys Let, 2003, 82,2422 Hes
appl. Phys. Lett. 2003,
83, 569), its maximum current efficiency, up to every ampere of 40.9 Kan Tela, approaches the most effective value of current single-shot photosphere device current; The green device 5 maximum current efficiency of preparation reach 86.0 cd/A, and maximum power efficiency reaches 84.3 lm/W, are that current single-shot photosphere device effect is one of best; The orange optical device 6 maximum current efficiency of preparation reach 51.6 cd/A, and maximum power efficiency reaches 50.2 lm/W, is current single-shot photosphere device efficiency maximum.Therefore, compare with other material of main parts, the present invention will have pentanoic or the derivative diphenylamine unit and the triazole with electronic transmission performance of methoxyl group of hole transport performance, diphenyl phosphate oxygen or pyridines unit connect by take the mode that four aryl silicon are bridge, prepared a material of main part roughly the same time with high triplet and bipolar carrier transmission performance, the balance that is conducive to current carrier in device, has obtained good electroluminescent properties, is conducive to develop efficient full-color display.
Claims (4)
1. a phosphorescent light body material, comprise the cells D n with hole transport performance and the unit An with electronic transmission performance, it is characterized in that: the unit with hole transport performance and the unit with electronic transmission performance are connected by take the mode that four aryl silicon are bridge, and structure is shown below:
Wherein, D
nfor
A
nfor
2. an electro phosphorescent device, comprise glass, be attached to Conducting Glass layer on glass, the hole injection layer closing with Conducting Glass laminating, hole transmission layer with hole injection layer laminating, electronic barrier layer with hole transmission layer laminating, luminescent layer with electronic barrier layer laminating, electron transfer layer with luminescent layer laminating, cathode layer with electron transfer layer laminating, luminescent layer is comprised of material of main part and dopant material, it is characterized in that: the material of main part of luminescent layer is material of main part as claimed in claim 1.
3. electro phosphorescent device as claimed in claim 2, is characterized in that: dopant material for the FIr6 that sends out dark blue light, send out the sky FIrpic of blue light, the Ir of green light (ppy)
2or the Ir (fbi) that sends out light orange (acac)
2(acac).
4. electro phosphorescent device as claimed in claim 3, is characterized in that, doping ratio is respectively: FIr6 is 10wt%, and FIrpic is 8wt%, Ir (ppy)
2(acac) be 9wt%, Ir (fbi)
2(acac) be 8wt%.
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| JP2015117210A (en) * | 2013-12-19 | 2015-06-25 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | Silane compound and organic el element |
| CN105368445B (en) * | 2015-11-06 | 2017-06-27 | 山东盛华新材料科技股份有限公司 | A kind of electroluminescent organic material and preparation method thereof |
| CN105418667B (en) * | 2015-11-06 | 2018-03-13 | 山东盛华新材料科技股份有限公司 | A kind of derivative of silicon tetraphenyl and dibenzothiophenes and preparation method thereof |
| CN105367595B (en) * | 2015-11-06 | 2017-12-26 | 山东盛华新材料科技股份有限公司 | A kind of electroluminescent hole mobile material and preparation method thereof |
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